4-(4-Methoxy­phenyl­diazenyl)-2,6-di­methyl­phenol

The title compound, C₁₅H₁₆N₂O, has a trans configuration with respect to the diazene double bond, and is approximately planar in the solid state. The dihedral angle between the planes of the two aromatic rings is 8.33 (16)°. In the crystal structure, the mol­ecules are linked to one another, head-to-head, by the hydroxyl groups, forming intermolecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.131
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,6-Dimethyl-4-(4-methoxyphenyldiazenyl)phenol

Crystal data

C15H16N2O2	F(000) = 544
Mr = 256.30	Dx = 1.288 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7798 reflections
a = 17.049 (4) Å	θ = 2.5–29.2°
b = 4.154 (9) Å	µ = 0.09 mm^−1
c = 19.130 (4) Å	T = 293 K
β = 102.695 (4)°	Prism, orange
V = 1322 (3) Å^3	0.50 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD Diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	1747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −20→20
Tmin = 0.958, Tmax = 0.991	k = −4→4
6146 measured reflections	l = −22→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0627P)^2 + 0.2962P] where P = (Fo^2 + 2Fc^2)/3
2303 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.34051 (9)	0.3929 (4)	0.12277 (8)	0.0398 (4)
N2	0.38422 (9)	0.5242 (4)	0.08623 (8)	0.0395 (4)
O1	0.24741 (8)	0.6586 (4)	−0.20425 (7)	0.0406 (4)
H1	0.2657 (17)	0.828 (7)	−0.2261 (14)	0.085 (10)*
O2	0.45260 (8)	0.3574 (4)	0.41835 (7)	0.0467 (4)
C1	0.37420 (11)	0.3814 (5)	0.19771 (10)	0.0346 (5)
C2	0.33006 (11)	0.2123 (5)	0.23789 (10)	0.0385 (5)
H2	0.2834	0.1074	0.2148	0.046*
C3	0.35364 (11)	0.1951 (5)	0.31185 (10)	0.0369 (5)
H3	0.3232	0.0806	0.3382	0.044*
C4	0.42324 (11)	0.3516 (5)	0.34568 (10)	0.0348 (5)
C5	0.46847 (11)	0.5199 (5)	0.30550 (10)	0.0403 (5)
H5	0.5155	0.6228	0.3286	0.048*
C6	0.44468 (11)	0.5362 (5)	0.23235 (10)	0.0377 (5)
H6	0.4753	0.6497	0.2060	0.045*
C7	0.34732 (11)	0.5435 (5)	0.01159 (9)	0.0353 (5)
C8	0.27199 (11)	0.4171 (5)	−0.01892 (10)	0.0367 (5)
H8	0.2434	0.3057	0.0096	0.044*
C9	0.23916 (11)	0.4555 (5)	−0.09128 (10)	0.0342 (5)
C10	0.28343 (11)	0.6249 (4)	−0.13240 (9)	0.0318 (4)
C11	0.36013 (11)	0.7473 (5)	−0.10402 (10)	0.0346 (5)
C12	0.39044 (11)	0.7024 (5)	−0.03112 (10)	0.0372 (5)
H12	0.4413	0.7816	−0.0105	0.045*
C13	0.40618 (14)	0.2012 (6)	0.46172 (10)	0.0519 (6)
H13A	0.4328	0.2212	0.5113	0.062*
H13B	0.4004	−0.0225	0.4490	0.062*
H13C	0.3540	0.2994	0.4541	0.062*
C14	0.40802 (12)	0.9175 (5)	−0.14975 (10)	0.0432 (5)
H14A	0.4607	0.9648	−0.1217	0.052*
H14B	0.3815	1.1145	−0.1675	0.052*
H14C	0.4125	0.7823	−0.1894	0.052*
C15	0.15791 (11)	0.3196 (5)	−0.12481 (10)	0.0426 (5)
H15A	0.1246	0.4866	−0.1504	0.051*
H15B	0.1334	0.2351	−0.0880	0.051*
H15C	0.1639	0.1504	−0.1574	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0404 (9)	0.0427 (10)	0.0358 (9)	0.0022 (8)	0.0071 (7)	0.0034 (8)
N2	0.0393 (9)	0.0457 (10)	0.0337 (9)	0.0025 (8)	0.0084 (7)	0.0010 (8)
O1	0.0503 (8)	0.0399 (9)	0.0305 (7)	−0.0020 (7)	0.0064 (6)	−0.0002 (6)
O2	0.0489 (8)	0.0577 (10)	0.0319 (7)	−0.0054 (7)	0.0053 (6)	0.0011 (7)
C1	0.0340 (10)	0.0349 (11)	0.0350 (10)	0.0068 (9)	0.0073 (8)	0.0023 (8)
C2	0.0325 (10)	0.0412 (12)	0.0395 (11)	−0.0014 (9)	0.0033 (8)	0.0023 (9)
C3	0.0358 (10)	0.0370 (11)	0.0384 (11)	0.0007 (9)	0.0095 (8)	0.0054 (9)
C4	0.0351 (10)	0.0351 (11)	0.0333 (10)	0.0081 (9)	0.0055 (8)	0.0011 (8)
C5	0.0312 (10)	0.0450 (12)	0.0432 (11)	−0.0007 (9)	0.0049 (8)	0.0004 (10)
C6	0.0331 (10)	0.0436 (12)	0.0382 (11)	0.0017 (9)	0.0118 (9)	0.0039 (9)
C7	0.0345 (10)	0.0383 (11)	0.0330 (10)	0.0048 (9)	0.0070 (8)	−0.0009 (9)
C8	0.0387 (10)	0.0368 (11)	0.0368 (10)	0.0009 (9)	0.0128 (8)	0.0014 (9)
C9	0.0348 (10)	0.0321 (10)	0.0358 (10)	0.0044 (8)	0.0082 (8)	−0.0031 (8)
C10	0.0387 (10)	0.0293 (10)	0.0275 (9)	0.0063 (9)	0.0071 (8)	−0.0030 (8)
C11	0.0376 (10)	0.0316 (10)	0.0366 (10)	0.0031 (8)	0.0126 (8)	−0.0025 (8)
C12	0.0329 (10)	0.0384 (12)	0.0396 (11)	0.0000 (9)	0.0065 (8)	−0.0020 (9)
C13	0.0655 (14)	0.0580 (15)	0.0334 (11)	−0.0045 (12)	0.0135 (10)	0.0014 (10)
C14	0.0459 (11)	0.0465 (12)	0.0392 (11)	−0.0016 (10)	0.0134 (9)	0.0017 (10)
C15	0.0403 (11)	0.0464 (13)	0.0404 (11)	−0.0029 (10)	0.0073 (9)	−0.0004 (10)

Geometric parameters (Å, º)

N1—N2	1.253 (2)	C7—C8	1.392 (3)
N1—C1	1.423 (2)	C8—C9	1.384 (3)
N2—C7	1.431 (2)	C8—H8	0.9300
O1—C10	1.384 (2)	C9—C10	1.395 (3)
O1—H1	0.91 (3)	C9—C15	1.503 (3)
O2—C4	1.370 (2)	C10—C11	1.397 (3)
O2—C13	1.423 (3)	C11—C12	1.389 (3)
C1—C2	1.380 (3)	C11—C14	1.499 (3)
C1—C6	1.395 (3)	C12—H12	0.9300
C2—C3	1.385 (3)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C3—C4	1.383 (3)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.391 (3)	C14—H14B	0.9600
C5—C6	1.370 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C12	1.381 (3)	C15—H15C	0.9600
N2—N1—C1	114.74 (16)	C8—C9—C15	121.07 (17)
N1—N2—C7	113.34 (16)	C10—C9—C15	120.74 (16)
C10—O1—H1	114.4 (16)	O1—C10—C9	115.74 (16)
C4—O2—C13	117.22 (15)	O1—C10—C11	121.49 (16)
C2—C1—C6	119.22 (17)	C9—C10—C11	122.74 (16)
C2—C1—N1	115.42 (17)	C12—C11—C10	116.83 (17)
C6—C1—N1	125.30 (17)	C12—C11—C14	121.27 (17)
C1—C2—C3	121.59 (18)	C10—C11—C14	121.90 (17)
C1—C2—H2	119.2	C7—C12—C11	121.94 (17)
C3—C2—H2	119.2	C7—C12—H12	119.0
C4—C3—C2	118.71 (18)	C11—C12—H12	119.0
C4—C3—H3	120.6	O2—C13—H13A	109.5
C2—C3—H3	120.6	O2—C13—H13B	109.5
O2—C4—C3	124.60 (17)	H13A—C13—H13B	109.5
O2—C4—C5	115.36 (17)	O2—C13—H13C	109.5
C3—C4—C5	120.04 (17)	H13A—C13—H13C	109.5
C6—C5—C4	120.90 (18)	H13B—C13—H13C	109.5
C6—C5—H5	119.6	C11—C14—H14A	109.5
C4—C5—H5	119.6	C11—C14—H14B	109.5
C5—C6—C1	119.54 (18)	H14A—C14—H14B	109.5
C5—C6—H6	120.2	C11—C14—H14C	109.5
C1—C6—H6	120.2	H14A—C14—H14C	109.5
C12—C7—C8	119.63 (17)	H14B—C14—H14C	109.5
C12—C7—N2	116.28 (17)	C9—C15—H15A	109.5
C8—C7—N2	124.08 (17)	C9—C15—H15B	109.5
C9—C8—C7	120.61 (18)	H15A—C15—H15B	109.5
C9—C8—H8	119.7	C9—C15—H15C	109.5
C7—C8—H8	119.7	H15A—C15—H15C	109.5
C8—C9—C10	118.20 (17)	H15B—C15—H15C	109.5
C1—N1—N2—C7	−177.60 (16)	C12—C7—C8—C9	−1.5 (3)
N2—N1—C1—C2	−174.43 (17)	N2—C7—C8—C9	177.73 (17)
N2—N1—C1—C6	8.4 (3)	C7—C8—C9—C10	−0.3 (3)
C6—C1—C2—C3	0.6 (3)	C7—C8—C9—C15	179.94 (18)
N1—C1—C2—C3	−176.72 (17)	C8—C9—C10—O1	−179.42 (16)
C1—C2—C3—C4	−0.1 (3)	C15—C9—C10—O1	0.4 (3)
C13—O2—C4—C3	−2.5 (3)	C8—C9—C10—C11	2.1 (3)
C13—O2—C4—C5	177.09 (18)	C15—C9—C10—C11	−178.09 (17)
C2—C3—C4—O2	179.05 (18)	O1—C10—C11—C12	179.53 (16)
C2—C3—C4—C5	−0.5 (3)	C9—C10—C11—C12	−2.1 (3)
O2—C4—C5—C6	−178.98 (17)	O1—C10—C11—C14	−0.8 (3)
C3—C4—C5—C6	0.6 (3)	C9—C10—C11—C14	177.57 (18)
C4—C5—C6—C1	−0.1 (3)	C8—C7—C12—C11	1.5 (3)
C2—C1—C6—C5	−0.5 (3)	N2—C7—C12—C11	−177.77 (17)
N1—C1—C6—C5	176.55 (18)	C10—C11—C12—C7	0.2 (3)
N1—N2—C7—C12	176.39 (17)	C14—C11—C12—C7	−179.42 (19)
N1—N2—C7—C8	−2.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^i	0.91 (3)	1.89 (3)	2.730 (4)	152 (2)

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