3,5-Di­methyl-4-(2,4,6-tri­methyl­phenyl­diazenyl)­phenol

In the title compound, C₁₇H₂₀N₂O, (I), the dihedral angle between the two phenyl rings is 15.69 (6)°. An intermolecular hydrogen-bonding association exists between the hydroxy group and one of the azo N atoms.

Computing details

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: Xtal3.2 (Hall et al., 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

4-(2,4,6-Trimethyl)phenylazo(3,5-dimethyl)phenol

Crystal data

C17H20N2O	F(000) = 576
Mr = 268.35	Dx = 1.250 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.369 (2) Å	Cell parameters from 25 reflections
b = 7.6809 (3) Å	θ = 6–14°
c = 15.332 (3) Å	µ = 0.08 mm^−1
β = 101.842 (9)°	T = 298 K
V = 1425.6 (4) Å^3	Block, red
Z = 4	0.47 × 0.47 × 0.47 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −5→14
2θ/ω scans	k = −4→9
2679 measured reflections	l = −18→17
2512 independent reflections	3 standard reflections every 200 reflections
1717 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0632P)^2 + 0.3065P] where P = (Fo^2 + 2Fc^2)/3
2512 reflections	(Δ/σ)max = 0.005
209 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.2961 (0.0094) x + 7.0530 (0.0028) y + 6.0601 (0.0114) z = 0.3356 (0.0068)

* 0.0269 (0.0013) C1 * 0.0005 (0.0013) C2 * -0.0222 (0.0014) C3 * 0.0159 (0.0014) C4 * 0.0120 (0.0014) C5 * -0.0331 (0.0013) C6 - 0.0865 (0.0034) C21 - 0.1788 (0.0034) C61 0.0308 (0.0029) O1 - 0.0599 (0.0028) N1

Rms deviation of fitted atoms = 0.0212

2.0913 (0.0094) x - 7.5108 (0.0019) y - 2.3827 (0.0125) z = 0.1199 (0.0111)

Angle to previous plane (with approximate e.s.d.) = 15.69 (0.06)

* 0.0071 (0.0013) C7 * 0.0035 (0.0013) C8 * -0.0091 (0.0014) C9 * 0.0036 (0.0014) C10 * 0.0072 (0.0014) C11 * -0.0124 (0.0014) C12 - 0.0283 (0.0033) C81 0.0190 (0.0036) C101 - 0.0108 (0.0040) C121 - 0.0198 (0.0028) N2

Rms deviation of fitted atoms = 0.0078

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.53687 (12)	−0.0420 (2)	0.22413 (11)	0.0590 (5)
H1	0.552 (2)	−0.103 (4)	0.2731 (17)	0.085 (9)*
N1	0.89937 (13)	0.1363 (2)	0.07926 (9)	0.0397 (4)
N2	0.97766 (12)	0.2192 (2)	0.12515 (10)	0.0388 (4)
C1	0.81126 (15)	0.0945 (2)	0.12329 (11)	0.0365 (4)
C2	0.82765 (15)	0.0203 (3)	0.20881 (12)	0.0388 (5)
C21	0.94033 (16)	−0.0194 (3)	0.26474 (14)	0.0529 (6)
H21	0.9894	−0.0526	0.2266	0.068 (7)*
H22	0.9344	−0.1130	0.3050	0.076 (8)*
H23	0.9688	0.0823	0.2982	0.072 (8)*
C3	0.73567 (16)	−0.0281 (3)	0.24174 (12)	0.0421 (5)
H3	0.7456	−0.0802	0.2976	0.047 (6)*
C4	0.62962 (15)	−0.0008 (3)	0.19358 (12)	0.0421 (5)
C5	0.61505 (16)	0.0692 (3)	0.10833 (12)	0.0432 (5)
H5	0.5439	0.0881	0.0758	0.048 (6)*
C6	0.70404 (15)	0.1111 (2)	0.07118 (12)	0.0388 (5)
C61	0.68632 (17)	0.1697 (3)	−0.02481 (13)	0.0516 (6)
H61	0.7171	0.2838	−0.0274	0.071 (7)*
H62	0.6086	0.1727	−0.0501	0.069 (7)*
H63	0.7220	0.0897	−0.0579	0.089 (9)*
C7	1.06864 (15)	0.2543 (2)	0.08298 (12)	0.0364 (4)
C8	1.05930 (15)	0.2815 (2)	−0.00945 (12)	0.0381 (4)
C81	0.95173 (16)	0.2771 (3)	−0.07651 (12)	0.0472 (5)
H81	0.9626	0.3239	−0.1321	0.051 (6)*
H82	0.8977	0.3455	−0.0550	0.062 (7)*
H83	0.9264	0.1590	−0.0851	0.055 (6)*
C9	1.15469 (16)	0.3193 (3)	−0.03952 (13)	0.0427 (5)
H9	1.1493	0.3394	−0.1001	0.039 (5)*
C10	1.25801 (16)	0.3286 (3)	0.01646 (13)	0.0434 (5)
C101	1.35980 (18)	0.3666 (4)	−0.02048 (17)	0.0594 (6)
H101	1.3667	0.2810	−0.0646	0.132 (13)*
H102	1.4240	0.3628	0.0269	0.120 (11)*
H103	1.3534	0.4802	−0.0472	0.141 (14)*
C11	1.26454 (16)	0.3014 (3)	0.10639 (13)	0.0470 (5)
H11	1.3333	0.3062	0.1448	0.061 (7)*
C12	1.17204 (15)	0.2672 (3)	0.14124 (12)	0.0422 (5)
C121	1.18669 (18)	0.2395 (4)	0.24080 (13)	0.0632 (7)
H121	1.2623	0.2610	0.2690	0.091 (9)*
H122	1.1676	0.1217	0.2522	0.139 (14)*
H123	1.1395	0.3182	0.2643	0.128 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0452 (8)	0.0788 (12)	0.0553 (9)	−0.0085 (8)	0.0153 (7)	0.0175 (9)
N1	0.0442 (9)	0.0411 (9)	0.0344 (8)	−0.0028 (7)	0.0096 (7)	0.0006 (7)
N2	0.0381 (8)	0.0440 (9)	0.0336 (8)	0.0008 (7)	0.0059 (7)	−0.0012 (7)
C1	0.0431 (10)	0.0355 (10)	0.0320 (9)	−0.0008 (8)	0.0106 (8)	−0.0037 (8)
C2	0.0425 (11)	0.0385 (11)	0.0352 (10)	0.0005 (8)	0.0078 (8)	−0.0009 (8)
C21	0.0469 (12)	0.0667 (15)	0.0456 (12)	0.0059 (11)	0.0106 (10)	0.0167 (12)
C3	0.0503 (11)	0.0421 (11)	0.0339 (10)	−0.0018 (9)	0.0089 (8)	0.0046 (8)
C4	0.0445 (11)	0.0423 (11)	0.0414 (10)	−0.0072 (9)	0.0135 (9)	−0.0001 (9)
C5	0.0407 (11)	0.0448 (12)	0.0411 (11)	−0.0053 (9)	0.0016 (9)	0.0000 (9)
C6	0.0459 (11)	0.0356 (10)	0.0340 (9)	−0.0054 (8)	0.0058 (8)	−0.0025 (8)
C61	0.0520 (13)	0.0597 (14)	0.0400 (11)	−0.0084 (11)	0.0023 (10)	0.0071 (10)
C7	0.0385 (10)	0.0369 (10)	0.0356 (9)	0.0004 (8)	0.0116 (8)	−0.0045 (8)
C8	0.0437 (11)	0.0369 (10)	0.0343 (9)	0.0002 (8)	0.0095 (8)	−0.0030 (8)
C81	0.0504 (12)	0.0570 (14)	0.0344 (10)	−0.0053 (10)	0.0093 (9)	0.0035 (9)
C9	0.0513 (12)	0.0425 (12)	0.0372 (10)	−0.0017 (9)	0.0157 (9)	−0.0022 (8)
C10	0.0447 (11)	0.0392 (11)	0.0492 (11)	0.0013 (9)	0.0167 (9)	−0.0039 (9)
C101	0.0500 (13)	0.0676 (17)	0.0675 (15)	−0.0028 (11)	0.0283 (12)	−0.0030 (13)
C11	0.0378 (11)	0.0527 (13)	0.0499 (12)	0.0011 (9)	0.0073 (9)	−0.0043 (10)
C12	0.0406 (11)	0.0474 (12)	0.0385 (10)	0.0026 (9)	0.0079 (8)	−0.0010 (9)
C121	0.0452 (13)	0.103 (2)	0.0387 (11)	−0.0004 (13)	0.0012 (9)	0.0057 (12)

Geometric parameters (Å, º)

O1—C4	1.362 (2)	C7—C12	1.405 (3)
O1—H1	0.87 (3)	C7—C8	1.414 (2)
N1—N2	1.249 (2)	C8—C9	1.383 (3)
N1—C1	1.431 (2)	C8—C81	1.506 (3)
N2—C7	1.434 (2)	C81—H81	0.9600
C1—C2	1.406 (2)	C81—H82	0.9600
C1—C6	1.407 (3)	C81—H83	0.9600
C2—C3	1.387 (3)	C9—C10	1.387 (3)
C2—C21	1.510 (3)	C9—H9	0.9300
C21—H21	0.9600	C10—C11	1.380 (3)
C21—H22	0.9600	C10—C101	1.511 (3)
C21—H23	0.9600	C101—H101	0.9600
C3—C4	1.383 (3)	C101—H102	0.9600
C3—H3	0.9300	C101—H103	0.9600
C4—C5	1.391 (3)	C11—C12	1.384 (3)
C5—C6	1.377 (3)	C11—H11	0.9300
C5—H5	0.9300	C12—C121	1.515 (3)
C6—C61	1.511 (2)	C121—H121	0.9600
C61—H61	0.9600	C121—H122	0.9600
C61—H62	0.9600	C121—H123	0.9600
C61—H63	0.9600
C4—O1—H1	112.0 (17)	C8—C7—N2	124.73 (16)
N2—N1—C1	115.22 (14)	C9—C8—C7	117.74 (17)
N1—N2—C7	115.57 (14)	C9—C8—C81	118.16 (16)
C2—C1—C6	120.35 (17)	C7—C8—C81	124.07 (16)
C2—C1—N1	123.55 (16)	C8—C81—H81	109.5
C6—C1—N1	115.61 (15)	C8—C81—H82	109.5
C3—C2—C1	118.44 (17)	H81—C81—H82	109.5
C3—C2—C21	118.00 (17)	C8—C81—H83	109.5
C1—C2—C21	123.46 (17)	H81—C81—H83	109.5
C2—C21—H21	109.5	H82—C81—H83	109.5
C2—C21—H22	109.5	C8—C9—C10	123.04 (18)
H21—C21—H22	109.5	C8—C9—H9	118.5
C2—C21—H23	109.5	C10—C9—H9	118.5
H21—C21—H23	109.5	C11—C10—C9	117.89 (17)
H22—C21—H23	109.5	C11—C10—C101	121.41 (19)
C4—C3—C2	121.61 (17)	C9—C10—C101	120.70 (19)
C4—C3—H3	119.2	C10—C101—H101	109.5
C2—C3—H3	119.2	C10—C101—H102	109.5
O1—C4—C3	123.69 (17)	H101—C101—H102	109.5
O1—C4—C5	117.20 (17)	C10—C101—H103	109.5
C3—C4—C5	119.10 (18)	H101—C101—H103	109.5
C6—C5—C4	121.24 (17)	H102—C101—H103	109.5
C6—C5—H5	119.4	C10—C11—C12	122.07 (18)
C4—C5—H5	119.4	C10—C11—H11	119.0
C5—C6—C1	118.97 (17)	C12—C11—H11	119.0
C5—C6—C61	120.25 (17)	C11—C12—C7	119.00 (17)
C1—C6—C61	120.77 (17)	C11—C12—C121	118.58 (18)
C6—C61—H61	109.5	C7—C12—C121	122.39 (17)
C6—C61—H62	109.5	C12—C121—H121	109.5
H61—C61—H62	109.5	C12—C121—H122	109.5
C6—C61—H63	109.5	H121—C121—H122	109.5
H61—C61—H63	109.5	C12—C121—H123	109.5
H62—C61—H63	109.5	H121—C121—H123	109.5
C12—C7—C8	120.22 (16)	H122—C121—H123	109.5
C12—C7—N2	115.01 (15)
C1—N1—N2—C7	177.16 (15)	N1—N2—C7—C12	−150.46 (17)
N2—N1—C1—C2	−48.4 (3)	N1—N2—C7—C8	31.8 (3)
N2—N1—C1—C6	139.63 (17)	C12—C7—C8—C9	0.5 (3)
C6—C1—C2—C3	−3.0 (3)	N2—C7—C8—C9	178.08 (18)
N1—C1—C2—C3	−174.63 (17)	C12—C7—C8—C81	−177.63 (19)
C6—C1—C2—C21	173.29 (19)	N2—C7—C8—C81	−0.1 (3)
N1—C1—C2—C21	1.6 (3)	C7—C8—C9—C10	1.1 (3)
C1—C2—C3—C4	−1.7 (3)	C81—C8—C9—C10	179.31 (19)
C21—C2—C3—C4	−178.19 (19)	C8—C9—C10—C11	−1.1 (3)
C2—C3—C4—O1	−178.22 (19)	C8—C9—C10—C101	178.7 (2)
C2—C3—C4—C5	3.1 (3)	C9—C10—C11—C12	−0.5 (3)
O1—C4—C5—C6	−178.53 (18)	C101—C10—C11—C12	179.7 (2)
C3—C4—C5—C6	0.2 (3)	C10—C11—C12—C7	2.0 (3)
C4—C5—C6—C1	−4.8 (3)	C10—C11—C12—C121	−179.8 (2)
C4—C5—C6—C61	173.73 (19)	C8—C7—C12—C11	−2.0 (3)
C2—C1—C6—C5	6.2 (3)	N2—C7—C12—C11	−179.81 (17)
N1—C1—C6—C5	178.47 (17)	C8—C7—C12—C121	179.9 (2)
C2—C1—C6—C61	−172.33 (18)	N2—C7—C12—C121	2.1 (3)
N1—C1—C6—C61	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.87 (3)	2.16 (3)	2.985 (2)	157 (2)

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.