N-(2-Hydroxy-ethyl)-2-[3-(p-tol-yl)triazen-1-yl]benzamide.

In the solid state, the structure of the title compound, C(16)H(18)N(4)O(2), is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds. These hydrogen bonds arrange the mol-ecules into a double-layer supra-molecular structure. The mol-ecular conformation is is consolidated by an intra-molecular N-H⋯N hydrogen bond. The dihedral angle between the aromatic rings is 8.01 (10)°

Related literature

For the synthesis of new ligands to stabilize dinuclear complexes and control their reactivity, see: Das et al. (2008 ▶); Estevan et al. (2006 ▶); Jie et al. (2007 ▶); Müller & Vogt (2007 ▶); Schilling et al. (2008 ▶). For the synthesis of 1,3-bis­(ar­yl)triazenes as precursors for triazenido ligands bearing Lewis basic ortho substituents such as ester, meth­oxy and methyl­mercapto groups, see: Nuricumbo-Escobar et al.(2007 ▶); Ríos-Moreno et al. (2003 ▶); Rodríguez et al. (1999 ▶); Tejel et al. (2004 ▶). The starting material 2-[4,5-dihydro-1,3-oxazol-2-yl]aniline was synthesized by a modification of the literature method of Gómez et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶); Orpen et al. (1989 ▶).

Experimental

Crystal data

C16H18N4O2

M = 298.34

Monoclinic,

a = 16.846 (2) Å

b = 12.2053 (17) Å

c = 7.4302 (11) Å

β = 93.212 (13)°

V = 1525.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.22 × 0.14 mm

Data collection

Bruker P4 diffractometer

Absorption correction: none

4153 measured reflections

3067 independent reflections

1778 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections every 97 reflections intensity decay: 2.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.188

S = 1.04

3067 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.22 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011908/kp2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011908/kp2210Isup2.hkl

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

C16H18N4O2	F(000) = 632
Mr = 298.34	Dx = 1.299 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 76 reflections
a = 16.846 (2) Å	θ = 4.7–12.0°
b = 12.2053 (17) Å	µ = 0.09 mm−1
c = 7.4302 (11) Å	T = 298 K
β = 93.212 (13)°	Neele, yellow
V = 1525.3 (4) Å3	0.40 × 0.22 × 0.14 mm
Z = 4

Bruker P4 diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 26.3°, θmin = 2.1°
graphite	h = −20→20
2θ/ω scans	k = −15→1
4153 measured reflections	l = −9→1
3067 independent reflections	3 standard reflections every 97 reflections
1778 reflections with I > 2σ(I)	intensity decay: 2.8%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.188	w = 1/[σ2(Fo2) + (0.1035P)2 + 0.0651P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3067 reflections	Δρmax = 0.57 e Å−3
201 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (3)

	x	y	z	Uiso*/Ueq
N1	0.69940 (11)	0.33793 (15)	−0.0017 (3)	0.0484 (5)
N2	0.76320 (11)	0.39013 (16)	0.0332 (3)	0.0481 (5)
N4	0.54570 (10)	0.30472 (15)	−0.1084 (3)	0.0456 (5)
H4A	0.5790	0.3480	−0.0525	0.055*
O1	0.51316 (10)	0.13062 (14)	−0.1750 (2)	0.0574 (5)
O2	0.39653 (10)	0.39859 (16)	0.0593 (3)	0.0651 (6)
H2B	0.4341	0.3834	0.1299	0.098*
N3	0.75322 (11)	0.49670 (16)	0.0124 (3)	0.0521 (6)
H3A	0.7066	0.5219	−0.0175	0.063*
C1	0.70741 (13)	0.22274 (19)	0.0146 (3)	0.0434 (6)
C2	0.64042 (13)	0.15801 (18)	−0.0313 (3)	0.0424 (6)
C3	0.64717 (15)	0.0445 (2)	−0.0087 (4)	0.0550 (7)
H3B	0.6029	0.0006	−0.0346	0.066*
C4	0.71719 (17)	−0.0036 (2)	0.0504 (4)	0.0646 (8)
H4B	0.7200	−0.0792	0.0651	0.078*
C5	0.78345 (15)	0.0601 (2)	0.0881 (4)	0.0654 (8)
H5A	0.8317	0.0275	0.1237	0.078*
C6	0.77816 (14)	0.1716 (2)	0.0729 (4)	0.0577 (7)
H6A	0.8228	0.2141	0.1022	0.069*
C7	0.81680 (13)	0.56925 (19)	0.0379 (3)	0.0472 (6)
C8	0.80588 (14)	0.6767 (2)	−0.0132 (4)	0.0552 (7)
H8A	0.7569	0.6993	−0.0642	0.066*
C9	0.86733 (16)	0.7513 (2)	0.0109 (4)	0.0608 (7)
H9A	0.8588	0.8240	−0.0227	0.073*
C10	0.94103 (16)	0.7200 (3)	0.0839 (4)	0.0622 (8)
C11	0.95105 (16)	0.6126 (3)	0.1297 (4)	0.0682 (8)
H11A	1.0006	0.5896	0.1771	0.082*
C12	0.89054 (14)	0.5364 (2)	0.1086 (4)	0.0608 (7)
H12A	0.8994	0.4637	0.1416	0.073*
C13	0.56158 (13)	0.19811 (19)	−0.1101 (3)	0.0420 (5)
C14	0.47468 (13)	0.3509 (2)	−0.1968 (3)	0.0495 (6)
H14A	0.4671	0.3186	−0.3157	0.059*
H14B	0.4829	0.4289	−0.2126	0.059*
C15	0.40087 (15)	0.3347 (2)	−0.0995 (4)	0.0617 (8)
H15A	0.3555	0.3523	−0.1806	0.074*
H15B	0.3968	0.2580	−0.0676	0.074*
C16	1.0073 (2)	0.8027 (3)	0.1157 (5)	0.0921 (11)
H16A	1.0569	0.7649	0.1374	0.138*
H16B	0.9968	0.8470	0.2184	0.138*
H16C	1.0101	0.8486	0.0113	0.138*

	U11	U22	U33	U12	U13	U23
N1	0.0424 (10)	0.0407 (11)	0.0617 (13)	−0.0019 (9)	0.0007 (9)	−0.0026 (9)
N2	0.0432 (11)	0.0418 (11)	0.0585 (13)	−0.0002 (9)	−0.0026 (9)	−0.0039 (9)
N4	0.0368 (10)	0.0412 (11)	0.0581 (13)	0.0021 (8)	−0.0039 (9)	−0.0023 (9)
O1	0.0554 (10)	0.0464 (10)	0.0678 (12)	−0.0062 (8)	−0.0189 (9)	−0.0037 (8)
O2	0.0477 (10)	0.0882 (14)	0.0579 (12)	0.0226 (9)	−0.0101 (8)	−0.0129 (10)
N3	0.0373 (10)	0.0382 (11)	0.0796 (15)	0.0020 (8)	−0.0072 (10)	−0.0020 (10)
C1	0.0409 (12)	0.0430 (13)	0.0461 (13)	0.0018 (10)	0.0015 (10)	0.0002 (10)
C2	0.0438 (12)	0.0405 (13)	0.0428 (13)	0.0027 (10)	0.0001 (10)	−0.0001 (10)
C3	0.0560 (15)	0.0425 (14)	0.0654 (17)	−0.0017 (11)	−0.0071 (12)	−0.0009 (12)
C4	0.0697 (18)	0.0407 (14)	0.082 (2)	0.0094 (13)	−0.0100 (15)	0.0012 (14)
C5	0.0509 (15)	0.0536 (16)	0.090 (2)	0.0143 (12)	−0.0097 (14)	0.0021 (15)
C6	0.0426 (13)	0.0525 (16)	0.0771 (19)	0.0020 (11)	−0.0053 (12)	0.0019 (13)
C7	0.0385 (12)	0.0428 (13)	0.0603 (15)	−0.0017 (10)	0.0020 (11)	−0.0070 (11)
C8	0.0420 (13)	0.0508 (15)	0.0726 (18)	0.0000 (11)	0.0029 (12)	0.0010 (13)
C9	0.0587 (16)	0.0510 (16)	0.0737 (18)	−0.0109 (12)	0.0113 (14)	−0.0017 (13)
C10	0.0525 (15)	0.0679 (18)	0.0669 (18)	−0.0196 (13)	0.0083 (13)	−0.0146 (15)
C11	0.0412 (14)	0.078 (2)	0.084 (2)	−0.0023 (13)	−0.0095 (13)	−0.0153 (17)
C12	0.0469 (14)	0.0481 (14)	0.086 (2)	0.0037 (12)	−0.0122 (13)	−0.0078 (14)
C13	0.0422 (12)	0.0436 (13)	0.0398 (12)	−0.0002 (10)	−0.0004 (10)	0.0004 (10)
C14	0.0487 (14)	0.0481 (14)	0.0508 (15)	0.0031 (11)	−0.0051 (11)	0.0011 (11)
C15	0.0456 (14)	0.0737 (19)	0.0643 (18)	0.0056 (13)	−0.0097 (12)	0.0006 (15)
C16	0.073 (2)	0.103 (3)	0.100 (3)	−0.043 (2)	0.0043 (18)	−0.016 (2)

N1—N2	1.264 (3)	C6—H6A	0.9300
N1—C1	1.417 (3)	C7—C8	1.375 (4)
N2—N3	1.319 (3)	C7—C12	1.381 (3)
N4—C13	1.329 (3)	C8—C9	1.383 (3)
N4—C14	1.447 (3)	C8—H8A	0.9300
N4—H4A	0.8600	C9—C10	1.381 (4)
O1—C13	1.238 (3)	C9—H9A	0.9300
O2—C15	1.420 (3)	C10—C11	1.363 (4)
O2—H2B	0.8200	C10—C16	1.513 (4)
N3—C7	1.395 (3)	C11—C12	1.382 (4)
N3—H3A	0.8600	C11—H11A	0.9300
C1—C6	1.393 (3)	C12—H12A	0.9300
C1—C2	1.404 (3)	C14—C15	1.486 (4)
C2—C3	1.400 (3)	C14—H14A	0.9700
C2—C13	1.503 (3)	C14—H14B	0.9700
C3—C4	1.368 (3)	C15—H15A	0.9700
C3—H3B	0.9300	C15—H15B	0.9700
C4—C5	1.376 (4)	C16—H16A	0.9600
C4—H4B	0.9300	C16—H16B	0.9600
C5—C6	1.367 (4)	C16—H16C	0.9600
C5—H5A	0.9300
N2—N1—C1	114.01 (19)	C10—C9—C8	121.2 (3)
N1—N2—N3	111.82 (19)	C10—C9—H9A	119.4
C13—N4—C14	122.64 (19)	C8—C9—H9A	119.4
C13—N4—H4A	118.7	C11—C10—C9	117.4 (2)
C14—N4—H4A	118.7	C11—C10—C16	121.5 (3)
C15—O2—H2B	109.5	C9—C10—C16	121.0 (3)
N2—N3—C7	121.21 (19)	C10—C11—C12	122.6 (3)
N2—N3—H3A	119.4	C10—C11—H11A	118.7
C7—N3—H3A	119.4	C12—C11—H11A	118.7
C6—C1—C2	119.0 (2)	C7—C12—C11	119.3 (3)
C6—C1—N1	123.2 (2)	C7—C12—H12A	120.3
C2—C1—N1	117.79 (19)	C11—C12—H12A	120.3
C3—C2—C1	118.0 (2)	O1—C13—N4	121.8 (2)
C3—C2—C13	115.7 (2)	O1—C13—C2	118.9 (2)
C1—C2—C13	126.3 (2)	N4—C13—C2	119.3 (2)
C4—C3—C2	121.7 (2)	N4—C14—C15	114.9 (2)
C4—C3—H3B	119.1	N4—C14—H14A	108.5
C2—C3—H3B	119.1	C15—C14—H14A	108.5
C3—C4—C5	119.9 (3)	N4—C14—H14B	108.5
C3—C4—H4B	120.1	C15—C14—H14B	108.5
C5—C4—H4B	120.1	H14A—C14—H14B	107.5
C6—C5—C4	119.8 (2)	O2—C15—C14	114.5 (2)
C6—C5—H5A	120.1	O2—C15—H15A	108.6
C4—C5—H5A	120.1	C14—C15—H15A	108.6
C5—C6—C1	121.5 (2)	O2—C15—H15B	108.6
C5—C6—H6A	119.3	C14—C15—H15B	108.6
C1—C6—H6A	119.3	H15A—C15—H15B	107.6
C8—C7—C12	119.1 (2)	C10—C16—H16A	109.5
C8—C7—N3	118.6 (2)	C10—C16—H16B	109.5
C12—C7—N3	122.3 (2)	H16A—C16—H16B	109.5
C7—C8—C9	120.3 (2)	C10—C16—H16C	109.5
C7—C8—H8A	119.8	H16A—C16—H16C	109.5
C9—C8—H8A	119.8	H16B—C16—H16C	109.5
C1—N1—N2—N3	178.6 (2)	N3—C7—C8—C9	179.6 (2)
N1—N2—N3—C7	−177.7 (2)	C7—C8—C9—C10	0.9 (4)
N2—N1—C1—C6	3.2 (3)	C8—C9—C10—C11	0.6 (4)
N2—N1—C1—C2	−176.6 (2)	C8—C9—C10—C16	−178.0 (3)
C6—C1—C2—C3	2.7 (3)	C9—C10—C11—C12	−1.2 (4)
N1—C1—C2—C3	−177.6 (2)	C16—C10—C11—C12	177.4 (3)
C6—C1—C2—C13	−174.8 (2)	C8—C7—C12—C11	1.3 (4)
N1—C1—C2—C13	5.0 (3)	N3—C7—C12—C11	179.8 (2)
C1—C2—C3—C4	−2.1 (4)	C10—C11—C12—C7	0.2 (5)
C13—C2—C3—C4	175.6 (2)	C14—N4—C13—O1	−6.1 (4)
C2—C3—C4—C5	−0.5 (4)	C14—N4—C13—C2	173.9 (2)
C3—C4—C5—C6	2.5 (5)	C3—C2—C13—O1	−11.0 (3)
C4—C5—C6—C1	−2.0 (5)	C1—C2—C13—O1	166.5 (2)
C2—C1—C6—C5	−0.7 (4)	C3—C2—C13—N4	169.0 (2)
N1—C1—C6—C5	179.5 (3)	C1—C2—C13—N4	−13.5 (3)
N2—N3—C7—C8	169.7 (2)	C13—N4—C14—C15	76.5 (3)
N2—N3—C7—C12	−8.8 (4)	N4—C14—C15—O2	71.8 (3)
C12—C7—C8—C9	−1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N1	0.86	2.05	2.696 (3)	132
O2—H2B···O1i	0.82	1.92	2.729 (2)	169
N3—H3A···O2ii	0.86	2.00	2.851 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N1	0.86	2.05	2.696 (3)	132
O2—H2B⋯O1i	0.82	1.92	2.729 (2)	169
N3—H3A⋯O2ii	0.86	2.00	2.851 (2)	170

Symmetry codes: (i) ; (ii) .