3-(2-Eth­oxy­phen­yl)-1-(3-nitro­phen­yl)triaz-1-ene

Melardi, M.R.; Ghannadan, A.; Peyman, M.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536811048781

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3485

https://doi.org/10.1107/S1600536811048781

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3-(2-Ethoxyphenyl)-1-(3-nitrophenyl)triaz-1-ene

Mohammad Reza Melardi,^a ^* Atefeh Ghannadan,^a Mitra Peyman,^a Giuseppe Bruno ^b and Hadi Amiri Rudbari ^b

^aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, and ^bDipartimento di Chimica Inorganica, Universita di Messina, Messina, Italy
^*Correspondence e-mail: m.melardi@kiau.ac.ir

(Received 4 November 2011; accepted 16 November 2011; online 30 November 2011)

The title compound, C₁₄H₁₄N₄O₃, exhibits a trans geometry about the N=N double bond in the triazene unit. The molecule is approximately planar (r.m.s. deviation = 0.044 Å for all non-H atoms). An intramolecular 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 R₂²(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_r = 286.29
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.06
3178 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) x, y, z+1; (ii) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048781/qm2042sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048781/qm2042Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048781/qm2042Isup3.cml

checkCIF report

Comment top

Aryl triazenes have been studied for over 130 years for their interesting structural, anticancer, and reactivity properties. The first extensive investigation of the coordination chemistry of a triazene derivative (1,3 diphenyltriazene) was carried out in 1887 by Meldola (Meldola et al., 1888). In the intervening years, numerous transition metal triazenide compounds have been studied (Leman et al., 1993). Triazene compounds characterized by having a diazoamino group commonly adopt a trans configuration in the ground state (Chen et al., 2002). The study of transition metal complexes containing 1,3-diaryltriazenide [RN═N—NR]- ligands has increased greatly in the past few years, because of their potential reactivity in relation to their several coordination modes (Vrieze et al., 1987). We have recently reported the synthesis and characterization of the two molecules 1,3-bis(2-methoxyphenyl)triazene (Rofouei, et al., 2006) and 1,3-bis(2-cyanophenyl)triazene (Melardi, et al., 2008).

The title compound, C₁₄H₁₄N₄O₃, is a related triazene compound. It exhibits a trans stereo chemistry of the N═N double bond, and the C9—N3—N2—N1 and C1—N1—N2—N3 torsion angles are -179.23 (9) and 177.91 (10)°, respectively which indicates the molecule is planar. The N1—N2 and N2—N3 bond distances are 1.3295 (13) and 1.2550 (14) Å, respectively, which indicates the presence of distinct single and double bonds between the nitrogen atoms. These values are in good agreement with the reported data for N—N and N═N bond distances (Hematyar, et al., 2008; Payehghadr, et al. 2007). For example, in 1,3-bis(2-cyanophenyl)triazene, the N—N and N═N bond distances are 1.335 (5) and 1.289 (5) Å (Melardi, et al., 2008). Individual molecules are mostly planar with an r.m.s. deviation from planarity of 0.044 Å for all non-hydrogen atoms. Every molecule in the molecular structure (Fig. 1) is connected to other unit by two distinct C—H···N hydrogen bonds to form dimers. The resultant dimers are then connected to each other by C—H···O hydrogen bonds to form infinite chains with R²₂(8) graph-set motifs (Grell et al., 2002)) (Fig. 2). Unit cell diagram of the title compound is illustrated in Fig. 3.

Related literature top

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 top

The compound was prepared by the following method: A 100 ml flask was charged with 10 g of ice and 15 ml of water and then cooled to 273 k in an ice-bath. To this was added 2 mmol (0.344 g) of 3-nitroaniline and 2 mmol of hydrochloric acid (36.5%) and 2 ml of water. To thissolution was then added a solution containing NaNO₂ (2 mmol, 0.16 g) in 2 ml of water during a 15 min period. After mixing for 15 min, the obtained solution was added to a solution of 2 mmol (0.261 ml) of o-phenetidin and 2 ml of methanol and 2 ml of water.

After that a solution containing 36 mmol (2.95 g) of sodium acetate in 10 ml of water was added. After mixing for 24 h the orange product was filtered off and dissolved in DMSO. Recrystallization from DMSO afforded the product as an orange crystalline material. ¹H NMR (300MHZ, DMSO): 1.37(6H, CH₃), 4.12(4H, CH₂), 6.98–8.07 (8H, aromatic), 12.93(1H, NH). IR (KBr): 3326, 1484, 1468, 1253, 1046, 816 cm^-1

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. C—H···N and C—H···O hydrogen bonds connect the different units into chains with R²₂(8) graph-set motifs
	Fig. 3. Unit cell packing diagram of the title compound, hydrogen bonding are shown as dashed lines.

3-(2-Ethoxyphenyl)-1-(3-nitrophenyl)triaz-1-ene top

Crystal data top

C₁₄H₁₄N₄O₃	Z = 2
M_r = 286.29	F(000) = 300
Triclinic, P1	D_x = 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

Data collection top

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

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) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0511P)² + 0.145P] where P = (F_o² + 2F_c²)/3
3178 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₄N₄O₃	γ = 90.192 (3)°
M_r = 286.29	V = 692.14 (6) Å³
Triclinic, P1	Z = 2
a = 6.7754 (4) Å	Mo Kα radiation
b = 7.5482 (4) Å	µ = 0.10 mm⁻¹
c = 14.0467 (7) Å	T = 293 K
α = 99.057 (3)°	0.55 × 0.33 × 0.26 mm
β = 102.479 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3178 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2693 reflections with I > 2σ(I)
T_min = 0.688, T_max = 0.746	R_int = 0.019
26097 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
3178 reflections	Δρ_min = −0.17 e Å⁻³
191 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₄O₃
M_r	286.29
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.7754 (4), 7.5482 (4), 14.0467 (7)
α, β, γ (°)	99.057 (3), 102.479 (2), 90.192 (3)
V (Å³)	692.14 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.33 × 0.26

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.688, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	26097, 3178, 2693
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.06
No. of reflections	3178
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.26	2.6130 (12)	104.9
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) x, y, z+1; (ii) −x+1, −y+1, −z+1.

References

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