Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022147/su6139sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022147/su6139Isup2.hkl
Contains datablock I

CCDC reference: 252993

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

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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 top
Crystal data top
C15H16N2O2F(000) = 544
Mr = 256.30Dx = 1.288 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7798 reflections
a = 17.049 (4) Åθ = 2.5–29.2°
b = 4.154 (9) ŵ = 0.09 mm1
c = 19.130 (4) ÅT = 293 K
β = 102.695 (4)°Prism, orange
V = 1322 (3) Å30.50 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD Diffractometer2303 independent reflections
Radiation source: fine-focus sealed tube1747 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 2020
Tmin = 0.958, Tmax = 0.991k = 44
6146 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0627P)2 + 0.2962P]
where P = (Fo2 + 2Fc2)/3
2303 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.34051 (9)0.3929 (4)0.12277 (8)0.0398 (4)
N20.38422 (9)0.5242 (4)0.08623 (8)0.0395 (4)
O10.24741 (8)0.6586 (4)0.20425 (7)0.0406 (4)
H10.2657 (17)0.828 (7)0.2261 (14)0.085 (10)*
O20.45260 (8)0.3574 (4)0.41835 (7)0.0467 (4)
C10.37420 (11)0.3814 (5)0.19771 (10)0.0346 (5)
C20.33006 (11)0.2123 (5)0.23789 (10)0.0385 (5)
H20.28340.10740.21480.046*
C30.35364 (11)0.1951 (5)0.31185 (10)0.0369 (5)
H30.32320.08060.33820.044*
C40.42324 (11)0.3516 (5)0.34568 (10)0.0348 (5)
C50.46847 (11)0.5199 (5)0.30550 (10)0.0403 (5)
H50.51550.62280.32860.048*
C60.44468 (11)0.5362 (5)0.23235 (10)0.0377 (5)
H60.47530.64970.20600.045*
C70.34732 (11)0.5435 (5)0.01159 (9)0.0353 (5)
C80.27199 (11)0.4171 (5)0.01892 (10)0.0367 (5)
H80.24340.30570.00960.044*
C90.23916 (11)0.4555 (5)0.09128 (10)0.0342 (5)
C100.28343 (11)0.6249 (4)0.13240 (9)0.0318 (4)
C110.36013 (11)0.7473 (5)0.10402 (10)0.0346 (5)
C120.39044 (11)0.7024 (5)0.03112 (10)0.0372 (5)
H120.44130.78160.01050.045*
C130.40618 (14)0.2012 (6)0.46172 (10)0.0519 (6)
H13A0.43280.22120.51130.062*
H13B0.40040.02250.44900.062*
H13C0.35400.29940.45410.062*
C140.40802 (12)0.9175 (5)0.14975 (10)0.0432 (5)
H14A0.46070.96480.12170.052*
H14B0.38151.11450.16750.052*
H14C0.41250.78230.18940.052*
C150.15791 (11)0.3196 (5)0.12481 (10)0.0426 (5)
H15A0.12460.48660.15040.051*
H15B0.13340.23510.08800.051*
H15C0.16390.15040.15740.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0404 (9)0.0427 (10)0.0358 (9)0.0022 (8)0.0071 (7)0.0034 (8)
N20.0393 (9)0.0457 (10)0.0337 (9)0.0025 (8)0.0084 (7)0.0010 (8)
O10.0503 (8)0.0399 (9)0.0305 (7)0.0020 (7)0.0064 (6)0.0002 (6)
O20.0489 (8)0.0577 (10)0.0319 (7)0.0054 (7)0.0053 (6)0.0011 (7)
C10.0340 (10)0.0349 (11)0.0350 (10)0.0068 (9)0.0073 (8)0.0023 (8)
C20.0325 (10)0.0412 (12)0.0395 (11)0.0014 (9)0.0033 (8)0.0023 (9)
C30.0358 (10)0.0370 (11)0.0384 (11)0.0007 (9)0.0095 (8)0.0054 (9)
C40.0351 (10)0.0351 (11)0.0333 (10)0.0081 (9)0.0055 (8)0.0011 (8)
C50.0312 (10)0.0450 (12)0.0432 (11)0.0007 (9)0.0049 (8)0.0004 (10)
C60.0331 (10)0.0436 (12)0.0382 (11)0.0017 (9)0.0118 (9)0.0039 (9)
C70.0345 (10)0.0383 (11)0.0330 (10)0.0048 (9)0.0070 (8)0.0009 (9)
C80.0387 (10)0.0368 (11)0.0368 (10)0.0009 (9)0.0128 (8)0.0014 (9)
C90.0348 (10)0.0321 (10)0.0358 (10)0.0044 (8)0.0082 (8)0.0031 (8)
C100.0387 (10)0.0293 (10)0.0275 (9)0.0063 (9)0.0071 (8)0.0030 (8)
C110.0376 (10)0.0316 (10)0.0366 (10)0.0031 (8)0.0126 (8)0.0025 (8)
C120.0329 (10)0.0384 (12)0.0396 (11)0.0000 (9)0.0065 (8)0.0020 (9)
C130.0655 (14)0.0580 (15)0.0334 (11)0.0045 (12)0.0135 (10)0.0014 (10)
C140.0459 (11)0.0465 (12)0.0392 (11)0.0016 (10)0.0134 (9)0.0017 (10)
C150.0403 (11)0.0464 (13)0.0404 (11)0.0029 (10)0.0073 (9)0.0004 (10)
Geometric parameters (Å, º) top
N1—N21.253 (2)C7—C81.392 (3)
N1—C11.423 (2)C8—C91.384 (3)
N2—C71.431 (2)C8—H80.9300
O1—C101.384 (2)C9—C101.395 (3)
O1—H10.91 (3)C9—C151.503 (3)
O2—C41.370 (2)C10—C111.397 (3)
O2—C131.423 (3)C11—C121.389 (3)
C1—C21.380 (3)C11—C141.499 (3)
C1—C61.395 (3)C12—H120.9300
C2—C31.385 (3)C13—H13A0.9600
C2—H20.9300C13—H13B0.9600
C3—C41.383 (3)C13—H13C0.9600
C3—H30.9300C14—H14A0.9600
C4—C51.391 (3)C14—H14B0.9600
C5—C61.370 (3)C14—H14C0.9600
C5—H50.9300C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C7—C121.381 (3)C15—H15C0.9600
N2—N1—C1114.74 (16)C8—C9—C15121.07 (17)
N1—N2—C7113.34 (16)C10—C9—C15120.74 (16)
C10—O1—H1114.4 (16)O1—C10—C9115.74 (16)
C4—O2—C13117.22 (15)O1—C10—C11121.49 (16)
C2—C1—C6119.22 (17)C9—C10—C11122.74 (16)
C2—C1—N1115.42 (17)C12—C11—C10116.83 (17)
C6—C1—N1125.30 (17)C12—C11—C14121.27 (17)
C1—C2—C3121.59 (18)C10—C11—C14121.90 (17)
C1—C2—H2119.2C7—C12—C11121.94 (17)
C3—C2—H2119.2C7—C12—H12119.0
C4—C3—C2118.71 (18)C11—C12—H12119.0
C4—C3—H3120.6O2—C13—H13A109.5
C2—C3—H3120.6O2—C13—H13B109.5
O2—C4—C3124.60 (17)H13A—C13—H13B109.5
O2—C4—C5115.36 (17)O2—C13—H13C109.5
C3—C4—C5120.04 (17)H13A—C13—H13C109.5
C6—C5—C4120.90 (18)H13B—C13—H13C109.5
C6—C5—H5119.6C11—C14—H14A109.5
C4—C5—H5119.6C11—C14—H14B109.5
C5—C6—C1119.54 (18)H14A—C14—H14B109.5
C5—C6—H6120.2C11—C14—H14C109.5
C1—C6—H6120.2H14A—C14—H14C109.5
C12—C7—C8119.63 (17)H14B—C14—H14C109.5
C12—C7—N2116.28 (17)C9—C15—H15A109.5
C8—C7—N2124.08 (17)C9—C15—H15B109.5
C9—C8—C7120.61 (18)H15A—C15—H15B109.5
C9—C8—H8119.7C9—C15—H15C109.5
C7—C8—H8119.7H15A—C15—H15C109.5
C8—C9—C10118.20 (17)H15B—C15—H15C109.5
C1—N1—N2—C7177.60 (16)C12—C7—C8—C91.5 (3)
N2—N1—C1—C2174.43 (17)N2—C7—C8—C9177.73 (17)
N2—N1—C1—C68.4 (3)C7—C8—C9—C100.3 (3)
C6—C1—C2—C30.6 (3)C7—C8—C9—C15179.94 (18)
N1—C1—C2—C3176.72 (17)C8—C9—C10—O1179.42 (16)
C1—C2—C3—C40.1 (3)C15—C9—C10—O10.4 (3)
C13—O2—C4—C32.5 (3)C8—C9—C10—C112.1 (3)
C13—O2—C4—C5177.09 (18)C15—C9—C10—C11178.09 (17)
C2—C3—C4—O2179.05 (18)O1—C10—C11—C12179.53 (16)
C2—C3—C4—C50.5 (3)C9—C10—C11—C122.1 (3)
O2—C4—C5—C6178.98 (17)O1—C10—C11—C140.8 (3)
C3—C4—C5—C60.6 (3)C9—C10—C11—C14177.57 (18)
C4—C5—C6—C10.1 (3)C8—C7—C12—C111.5 (3)
C2—C1—C6—C50.5 (3)N2—C7—C12—C11177.77 (17)
N1—C1—C6—C5176.55 (18)C10—C11—C12—C70.2 (3)
N1—N2—C7—C12176.39 (17)C14—C11—C12—C7179.42 (19)
N1—N2—C7—C82.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.91 (3)1.89 (3)2.730 (4)152 (2)
Symmetry code: (i) x+1/2, y+1/2, z1/2.
A comparisson of geometrical parameters (Å, °) for compound (I) and related compounds (II) and (III). top
Bonds(I)(II)(III)
C7—N21.431 (2)1.428 (3)1.424 (2)
N2—N11.253 (2)1.252 (3)1.256 (2)
N1—C11.423 (2)1.451 (3)1.430 (2)
C1—N1—N2—C7-177.53 (16)-178.00 (17)-177.66 (16)
(C1-C6) and C7N2N1C28.24 (26)13.48 (22)2.65 (15)
(C7-C12) and C7N2N1C24.29 (25)10.90 (21)2.84 (15)
(C1-C6) and (C7-C12)8.33 (16)6.57 (15)5.48 (10)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds