3-(2-Eth-oxy-phen-yl)-1-(3-nitro-phen-yl)triaz-1-ene.

The title compound, C(14)H(14)N(4)O(3), exhibits a trans geometry about the N=N double bond in the triazene unit. The mol-ecule is approximately planar (r.m.s. deviation = 0.044 Å for all non-H atoms). An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, C-H⋯N hydrogen bonds lead to the formation of dimers which are, in turn, connected to each other by C-H⋯O hydrogen bonds, forming infinite chains of R(2) (2)(8) graph-set motif.

Related literature

For aryl triazenes, their structural properties and metal complexes see: Meldola & Streatfield (1888 ▶); Leman et al. (1993 ▶); Chen et al. (2002 ▶); Vrieze & Van Koten (1987 ▶). For a similar structure with cyano instead of eth­oxy groups, see: Melardi et al. (2008 ▶). For the synthesis and characterization of a similar structure with meth­oxy instead of eth­oxy groups, see: Rofouei et al. (2006 ▶). For the synthesis and crystal structures of mercury(II) and silver(I) complexes with 1,3-bis­(2-meth­oxy­phen­yl)triazene, see: Hematyar & Rofouei (2008 ▶) and Payehghadr et al. (2007 ▶), respectively. For hydrogen-bond patterns and related graph sets, see: Grell et al. (2002 ▶).

Experimental

Crystal data

C14H14N4O3

M = 286.29

Triclinic,

a = 6.7754 (4) Å

b = 7.5482 (4) Å

c = 14.0467 (7) Å

α = 99.057 (3)°

β = 102.479 (2)°

γ = 90.192 (3)°

V = 692.14 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.55 × 0.33 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.688, T max = 0.746

26097 measured reflections

3178 independent reflections

2693 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.06

3178 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; 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 datablock(s) I, global. DOI: 10.1107/S1600536811048781/qm2042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048781/qm2042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048781/qm2042Isup3.cml

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

C14H14N4O3	Z = 2
Mr = 286.29	F(000) = 300
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7754 (4) Å	Cell parameters from 9946 reflections
b = 7.5482 (4) Å	θ = 2.7–31.1°
c = 14.0467 (7) Å	µ = 0.10 mm−1
α = 99.057 (3)°	T = 293 K
β = 102.479 (2)°	Irregular, colourless
γ = 90.192 (3)°	0.55 × 0.33 × 0.26 mm
V = 692.14 (6) Å3

Bruker APEXII CCD diffractometer	3178 independent reflections
Radiation source: fine-focus sealed tube	2693 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.688, Tmax = 0.746	k = −9→9
26097 measured reflections	l = −18→18

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) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.145P] where P = (Fo2 + 2Fc2)/3
3178 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.14363 (13)	0.78956 (13)	0.80767 (6)	0.0496 (2)
O2	−0.25541 (16)	0.75287 (19)	0.17852 (8)	0.0775 (4)
O3	−0.09609 (19)	0.67215 (19)	0.06405 (7)	0.0772 (4)
N1	0.08879 (15)	0.75248 (15)	0.61555 (7)	0.0463 (3)
H1	0.1969	0.7224	0.6532	0.056*
N2	0.07393 (15)	0.72890 (13)	0.51841 (7)	0.0405 (2)
N3	0.22616 (15)	0.65698 (14)	0.49393 (7)	0.0452 (2)
N4	−0.10788 (17)	0.69283 (16)	0.15046 (7)	0.0510 (3)
C8	0.3938 (2)	0.7498 (2)	0.94857 (10)	0.0657 (4)
H1A	0.3911	0.6227	0.9261	0.099*
H1B	0.4296	0.7732	1.0195	0.099*
H1C	0.4919	0.8082	0.9226	0.099*
C7	0.1898 (2)	0.8201 (2)	0.91353 (9)	0.0539 (3)
H2A	0.0890	0.7591	0.9376	0.065*
H2B	0.1895	0.9476	0.9383	0.065*
C2	−0.03776 (17)	0.84559 (16)	0.76042 (8)	0.0408 (3)
C1	−0.06778 (17)	0.82518 (15)	0.65747 (8)	0.0388 (2)
C9	0.21578 (17)	0.63226 (15)	0.39086 (8)	0.0383 (2)
C14	0.05175 (17)	0.67526 (15)	0.32130 (8)	0.0385 (2)
H6	−0.0627	0.7236	0.3402	0.046*
C13	0.06377 (18)	0.64406 (15)	0.22357 (8)	0.0404 (3)
C12	0.2299 (2)	0.57199 (18)	0.19153 (9)	0.0488 (3)
H8	0.2329	0.5523	0.1248	0.059*
C11	0.3909 (2)	0.53033 (18)	0.26185 (10)	0.0529 (3)
H9	0.5049	0.4818	0.2425	0.063*
C10	0.38486 (19)	0.55994 (17)	0.36067 (9)	0.0466 (3)
H10	0.4946	0.5313	0.4074	0.056*
C6	−0.24781 (19)	0.87423 (17)	0.60219 (10)	0.0483 (3)
H11	−0.2686	0.8599	0.5337	0.058*
C5	−0.3968 (2)	0.94460 (18)	0.64873 (11)	0.0551 (3)
H12	−0.5176	0.9778	0.6114	0.066*
C4	−0.3679 (2)	0.96581 (19)	0.74939 (12)	0.0565 (3)
H13	−0.4688	1.0137	0.7801	0.068*
C3	−0.1888 (2)	0.91623 (19)	0.80575 (10)	0.0514 (3)
H14	−0.1701	0.9304	0.8741	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0446 (5)	0.0738 (6)	0.0283 (4)	0.0085 (4)	0.0058 (3)	0.0050 (4)
O2	0.0549 (6)	0.1304 (11)	0.0483 (6)	0.0282 (6)	0.0088 (5)	0.0206 (6)
O3	0.0823 (8)	0.1176 (10)	0.0321 (5)	0.0152 (7)	0.0110 (5)	0.0155 (5)
N1	0.0432 (5)	0.0665 (7)	0.0277 (5)	0.0103 (5)	0.0052 (4)	0.0068 (4)
N2	0.0437 (5)	0.0473 (5)	0.0295 (5)	0.0021 (4)	0.0061 (4)	0.0060 (4)
N3	0.0461 (5)	0.0557 (6)	0.0329 (5)	0.0094 (4)	0.0074 (4)	0.0064 (4)
N4	0.0537 (6)	0.0657 (7)	0.0329 (5)	0.0009 (5)	0.0067 (4)	0.0096 (5)
C8	0.0646 (9)	0.0905 (11)	0.0386 (7)	0.0041 (8)	0.0004 (6)	0.0152 (7)
C7	0.0621 (8)	0.0705 (9)	0.0284 (6)	0.0037 (6)	0.0093 (5)	0.0069 (5)
C2	0.0415 (6)	0.0438 (6)	0.0360 (6)	−0.0011 (5)	0.0081 (4)	0.0035 (5)
C1	0.0398 (6)	0.0399 (6)	0.0357 (6)	0.0002 (4)	0.0072 (4)	0.0047 (4)
C9	0.0437 (6)	0.0379 (6)	0.0334 (5)	0.0025 (4)	0.0091 (4)	0.0058 (4)
C14	0.0408 (6)	0.0418 (6)	0.0338 (5)	0.0020 (4)	0.0103 (4)	0.0054 (4)
C13	0.0457 (6)	0.0422 (6)	0.0334 (6)	−0.0005 (5)	0.0083 (5)	0.0074 (4)
C12	0.0604 (7)	0.0534 (7)	0.0368 (6)	0.0060 (6)	0.0199 (5)	0.0068 (5)
C11	0.0557 (7)	0.0566 (8)	0.0524 (7)	0.0155 (6)	0.0247 (6)	0.0094 (6)
C10	0.0468 (6)	0.0493 (7)	0.0452 (6)	0.0114 (5)	0.0108 (5)	0.0109 (5)
C6	0.0466 (6)	0.0521 (7)	0.0434 (7)	0.0028 (5)	0.0024 (5)	0.0093 (5)
C5	0.0421 (6)	0.0523 (7)	0.0693 (9)	0.0062 (5)	0.0057 (6)	0.0137 (6)
C4	0.0476 (7)	0.0547 (8)	0.0704 (9)	0.0072 (6)	0.0228 (6)	0.0055 (6)
C3	0.0521 (7)	0.0577 (7)	0.0460 (7)	0.0018 (6)	0.0186 (6)	0.0019 (6)

O1—C2	1.3672 (14)	C1—C6	1.3828 (16)
O1—C7	1.4327 (14)	C9—C14	1.3886 (15)
O2—N4	1.2153 (15)	C9—C10	1.3898 (16)
O3—N4	1.2192 (14)	C14—C13	1.3760 (15)
N1—N2	1.3295 (13)	C14—H6	0.9300
N1—C1	1.3948 (15)	C13—C12	1.3824 (17)
N1—H1	0.8600	C12—C11	1.3782 (19)
N2—N3	1.2550 (14)	C12—H8	0.9300
N3—C9	1.4165 (14)	C11—C10	1.3803 (18)
N4—C13	1.4658 (16)	C11—H9	0.9300
C8—C7	1.493 (2)	C10—H10	0.9300
C8—H1A	0.9600	C6—C5	1.3813 (19)
C8—H1B	0.9600	C6—H11	0.9300
C8—H1C	0.9600	C5—C4	1.368 (2)
C7—H2A	0.9700	C5—H12	0.9300
C7—H2B	0.9700	C4—C3	1.386 (2)
C2—C3	1.3840 (17)	C4—H13	0.9300
C2—C1	1.3996 (16)	C3—H14	0.9300
C2—O1—C7	117.63 (9)	C10—C9—N3	115.61 (10)
N2—N1—C1	121.19 (9)	C13—C14—C9	117.92 (11)
N2—N1—H1	119.4	C13—C14—H6	121.0
C1—N1—H1	119.4	C9—C14—H6	121.0
N3—N2—N1	112.29 (9)	C14—C13—C12	123.37 (11)
N2—N3—C9	113.57 (9)	C14—C13—N4	117.84 (10)
O2—N4—O3	122.79 (12)	C12—C13—N4	118.78 (10)
O2—N4—C13	118.69 (10)	C11—C12—C13	117.71 (11)
O3—N4—C13	118.52 (11)	C11—C12—H8	121.1
C7—C8—H1A	109.5	C13—C12—H8	121.1
C7—C8—H1B	109.5	C12—C11—C10	120.67 (11)
H1A—C8—H1B	109.5	C12—C11—H9	119.7
C7—C8—H1C	109.5	C10—C11—H9	119.7
H1A—C8—H1C	109.5	C11—C10—C9	120.44 (11)
H1B—C8—H1C	109.5	C11—C10—H10	119.8
O1—C7—C8	108.27 (11)	C9—C10—H10	119.8
O1—C7—H2A	110.0	C5—C6—C1	119.94 (12)
C8—C7—H2A	110.0	C5—C6—H11	120.0
O1—C7—H2B	110.0	C1—C6—H11	120.0
C8—C7—H2B	110.0	C4—C5—C6	120.46 (12)
H2A—C7—H2B	108.4	C4—C5—H12	119.8
O1—C2—C3	125.54 (11)	C6—C5—H12	119.8
O1—C2—C1	115.09 (10)	C5—C4—C3	120.27 (12)
C3—C2—C1	119.37 (11)	C5—C4—H13	119.9
C6—C1—N1	123.10 (11)	C3—C4—H13	119.9
C6—C1—C2	119.87 (11)	C2—C3—C4	120.09 (12)
N1—C1—C2	117.02 (10)	C2—C3—H14	120.0
C14—C9—C10	119.88 (10)	C4—C3—H14	120.0
C14—C9—N3	124.50 (10)
C1—N1—N2—N3	−177.91 (10)	O2—N4—C13—C14	−2.37 (18)
N1—N2—N3—C9	−179.23 (9)	O3—N4—C13—C14	177.30 (12)
C2—O1—C7—C8	−179.64 (12)	O2—N4—C13—C12	178.57 (13)
C7—O1—C2—C3	−5.71 (19)	O3—N4—C13—C12	−1.77 (18)
C7—O1—C2—C1	175.15 (11)	C14—C13—C12—C11	−0.2 (2)
N2—N1—C1—C6	1.14 (18)	N4—C13—C12—C11	178.81 (12)
N2—N1—C1—C2	−179.72 (10)	C13—C12—C11—C10	0.1 (2)
O1—C2—C1—C6	178.70 (11)	C12—C11—C10—C9	0.1 (2)
C3—C2—C1—C6	−0.50 (18)	C14—C9—C10—C11	−0.06 (19)
O1—C2—C1—N1	−0.47 (16)	N3—C9—C10—C11	−179.95 (11)
C3—C2—C1—N1	−179.67 (11)	N1—C1—C6—C5	179.66 (12)
N2—N3—C9—C14	−2.50 (17)	C2—C1—C6—C5	0.54 (19)
N2—N3—C9—C10	177.40 (11)	C1—C6—C5—C4	−0.2 (2)
C10—C9—C14—C13	−0.07 (17)	C6—C5—C4—C3	−0.2 (2)
N3—C9—C14—C13	179.82 (10)	O1—C2—C3—C4	−179.01 (12)
C9—C14—C13—C12	0.20 (18)	C1—C2—C3—C4	0.1 (2)
C9—C14—C13—N4	−178.82 (10)	C5—C4—C3—C2	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.26	2.6130 (12)	105.
C7—H2A···O3i	0.97	2.55	3.4595 (18)	157
C10—H10···N3ii	0.93	2.65	3.543 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.26	2.6130 (12)	105
C7—H2A⋯O3i	0.97	2.55	3.4595 (18)	157
C10—H10⋯N3ii	0.93	2.65	3.543 (3)	161

Symmetry codes: (i) ; (ii) .