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The crystal structure of the title compound, C17H20N2O, determined at 208 K, shows that the mol­ecule is approx­imately planar in the solid state, having a trans configuration with respect to the azo double bond, as found for other diazene derivatives. The dihedral angle between the planes of the two aromatic rings is 5.04 (12)°. The hydroxy group and an N atom of the azo group are linked by an intramolecular O—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025261/ci6296sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025261/ci6296Isup2.hkl
Contains datablock I

CCDC reference: 227885

Key indicators

  • Single-crystal X-ray study
  • T = 208 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.089
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C13
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1543 Count of symmetry unique reflns 1545 Completeness (_total/calc) 99.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 2 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 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-tert-butyl-4-metyl-6-(phenyldiazenyl)phenol top
Crystal data top
C17H20N2OF(000) = 576
Mr = 268.35Dx = 1.204 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 12915 reflections
a = 6.2333 (7) Åθ = 2.2–31.8°
b = 10.4182 (12) ŵ = 0.08 mm1
c = 22.788 (3) ÅT = 208 K
V = 1479.8 (3) Å3Prism, orange
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Bruker AXS SMART CCD
diffractometer
1543 independent reflections
Radiation source: fine-focus sealed tube1355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 77
Tmin = 0.985, Tmax = 0.985k = 1210
8784 measured reflectionsl = 2327
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0448P)2 + 0.273P]
where P = (Fo2 + 2Fc2)/3
1543 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 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
O10.1895 (3)0.02999 (15)0.20142 (7)0.0379 (4)
H10.28840.04730.17910.057*
N10.4083 (3)0.01523 (19)0.10704 (8)0.0313 (5)
N20.2864 (3)0.06981 (18)0.08529 (8)0.0306 (4)
C10.5837 (4)0.0535 (2)0.07062 (10)0.0302 (5)
C20.6092 (4)0.0120 (2)0.01294 (10)0.0373 (6)
H20.50880.04260.00410.045*
C30.7857 (4)0.0528 (2)0.01870 (11)0.0427 (6)
H30.80470.02520.05720.051*
C40.9341 (4)0.1344 (3)0.00651 (12)0.0427 (7)
H41.05230.16140.01510.051*
C50.9083 (4)0.1761 (3)0.06334 (11)0.0420 (6)
H51.00860.23100.08020.050*
C60.7321 (4)0.1357 (2)0.09535 (11)0.0352 (6)
H60.71360.16410.13370.042*
C70.1107 (4)0.1087 (2)0.12009 (10)0.0285 (5)
C80.0638 (3)0.0609 (2)0.17689 (10)0.0274 (5)
C90.1172 (4)0.1071 (2)0.20728 (9)0.0264 (5)
C100.2438 (4)0.1969 (2)0.17856 (10)0.0301 (5)
H100.36380.22800.19820.036*
C110.2030 (4)0.2438 (2)0.12196 (10)0.0320 (5)
C120.0225 (4)0.1987 (2)0.09399 (10)0.0314 (5)
H120.01090.22930.05680.038*
C130.3528 (4)0.3379 (2)0.09345 (11)0.0404 (6)
H13A0.30030.35930.05510.061*
H13B0.49290.30030.09010.061*
H13C0.36110.41430.11690.061*
C140.1723 (4)0.0581 (2)0.26954 (10)0.0287 (5)
C150.2292 (4)0.0855 (2)0.26698 (11)0.0397 (6)
H15A0.26350.11550.30570.060*
H15B0.35070.09770.24170.060*
H15C0.10910.13280.25200.060*
C160.0164 (4)0.0798 (3)0.31134 (10)0.0419 (6)
H16A0.02060.04890.34970.063*
H16B0.13980.03420.29720.063*
H16C0.04830.16980.31340.063*
C170.3670 (4)0.1291 (2)0.29479 (11)0.0413 (6)
H17A0.39770.09690.33340.062*
H17B0.33610.21920.29700.062*
H17C0.48890.11560.26980.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0353 (9)0.0437 (9)0.0348 (9)0.0140 (8)0.0085 (8)0.0079 (7)
N10.0273 (10)0.0362 (11)0.0305 (10)0.0011 (9)0.0039 (9)0.0016 (8)
N20.0274 (9)0.0319 (10)0.0325 (10)0.0024 (9)0.0024 (8)0.0012 (8)
C10.0281 (11)0.0325 (12)0.0301 (12)0.0030 (11)0.0041 (10)0.0046 (9)
C20.0363 (13)0.0405 (13)0.0352 (13)0.0007 (12)0.0026 (11)0.0007 (11)
C30.0452 (15)0.0511 (15)0.0317 (13)0.0066 (15)0.0116 (12)0.0046 (11)
C40.0313 (13)0.0499 (15)0.0468 (16)0.0033 (12)0.0117 (12)0.0187 (13)
C50.0349 (14)0.0446 (15)0.0465 (16)0.0073 (13)0.0013 (12)0.0104 (12)
C60.0357 (13)0.0408 (13)0.0292 (12)0.0000 (12)0.0022 (11)0.0045 (10)
C70.0264 (11)0.0292 (12)0.0298 (12)0.0020 (11)0.0033 (10)0.0033 (9)
C80.0255 (11)0.0274 (11)0.0292 (11)0.0009 (10)0.0002 (9)0.0008 (9)
C90.0251 (11)0.0265 (11)0.0276 (11)0.0031 (10)0.0000 (10)0.0038 (9)
C100.0258 (11)0.0329 (11)0.0315 (12)0.0010 (11)0.0029 (10)0.0032 (10)
C110.0333 (12)0.0308 (12)0.0318 (13)0.0017 (12)0.0034 (11)0.0002 (9)
C120.0330 (12)0.0338 (12)0.0273 (12)0.0013 (11)0.0010 (10)0.0039 (10)
C130.0362 (14)0.0434 (14)0.0416 (14)0.0083 (12)0.0002 (12)0.0055 (12)
C140.0289 (11)0.0308 (11)0.0264 (11)0.0009 (10)0.0042 (10)0.0009 (9)
C150.0436 (14)0.0379 (13)0.0376 (14)0.0027 (12)0.0063 (12)0.0038 (11)
C160.0393 (14)0.0584 (16)0.0281 (12)0.0071 (13)0.0001 (11)0.0016 (12)
C170.0390 (14)0.0472 (15)0.0377 (14)0.0030 (12)0.0137 (12)0.0034 (11)
Geometric parameters (Å, º) top
O1—C81.350 (3)C10—C111.403 (3)
O1—H10.82C10—H100.93
N1—N21.268 (2)C11—C121.376 (3)
N1—C11.429 (3)C11—C131.502 (3)
N2—C71.411 (3)C12—H120.93
C1—C61.381 (3)C13—H13A0.96
C1—C21.393 (3)C13—H13B0.96
C2—C31.383 (3)C13—H13C0.96
C2—H20.93C14—C161.530 (3)
C3—C41.381 (4)C14—C171.533 (3)
C3—H30.93C14—C151.538 (3)
C4—C51.375 (4)C15—H15A0.96
C4—H40.93C15—H15B0.96
C5—C61.384 (3)C15—H15C0.96
C5—H50.93C16—H16A0.96
C6—H60.93C16—H16B0.96
C7—C121.387 (3)C16—H16C0.96
C7—C81.417 (3)C17—H17A0.96
C8—C91.409 (3)C17—H17B0.96
C9—C101.388 (3)C17—H17C0.96
C9—C141.546 (3)
C8—O1—H1109.5C10—C11—C13120.8 (2)
N2—N1—C1115.24 (19)C11—C12—C7121.5 (2)
N1—N2—C7116.48 (19)C11—C12—H12119.3
C6—C1—C2120.1 (2)C7—C12—H12119.3
C6—C1—N1116.6 (2)C11—C13—H13A109.5
C2—C1—N1123.3 (2)C11—C13—H13B109.5
C3—C2—C1119.2 (2)H13A—C13—H13B109.5
C3—C2—H2120.4C11—C13—H13C109.5
C1—C2—H2120.4H13A—C13—H13C109.5
C4—C3—C2120.4 (2)H13B—C13—H13C109.5
C4—C3—H3119.8C16—C14—C17107.66 (19)
C2—C3—H3119.8C16—C14—C15110.1 (2)
C5—C4—C3120.5 (2)C17—C14—C15107.5 (2)
C5—C4—H4119.7C16—C14—C9110.58 (18)
C3—C4—H4119.7C17—C14—C9111.16 (19)
C4—C5—C6119.6 (3)C15—C14—C9109.72 (18)
C4—C5—H5120.2C14—C15—H15A109.5
C6—C5—H5120.2C14—C15—H15B109.5
C1—C6—C5120.3 (2)H15A—C15—H15B109.5
C1—C6—H6119.8C14—C15—H15C109.5
C5—C6—H6119.8H15A—C15—H15C109.5
C12—C7—N2114.7 (2)H15B—C15—H15C109.5
C12—C7—C8120.4 (2)C14—C16—H16A109.5
N2—C7—C8124.9 (2)C14—C16—H16B109.5
O1—C8—C9120.07 (19)H16A—C16—H16B109.5
O1—C8—C7120.32 (19)C14—C16—H16C109.5
C9—C8—C7119.6 (2)H16A—C16—H16C109.5
C10—C9—C8117.0 (2)H16B—C16—H16C109.5
C10—C9—C14121.9 (2)C14—C17—H17A109.5
C8—C9—C14121.1 (2)C14—C17—H17B109.5
C9—C10—C11124.5 (2)H17A—C17—H17B109.5
C9—C10—H10117.8C14—C17—H17C109.5
C11—C10—H10117.8H17A—C17—H17C109.5
C12—C11—C10117.1 (2)H17B—C17—H17C109.5
C12—C11—C13122.1 (2)
C1—N1—N2—C7179.46 (19)C7—C8—C9—C101.3 (3)
N2—N1—C1—C6173.4 (2)O1—C8—C9—C141.7 (3)
N2—N1—C1—C26.6 (3)C7—C8—C9—C14179.46 (19)
C6—C1—C2—C30.8 (4)C8—C9—C10—C110.1 (3)
N1—C1—C2—C3179.1 (2)C14—C9—C10—C11179.3 (2)
C1—C2—C3—C40.4 (4)C9—C10—C11—C121.3 (3)
C2—C3—C4—C50.0 (4)C9—C10—C11—C13178.0 (2)
C3—C4—C5—C60.0 (4)C10—C11—C12—C71.4 (3)
C2—C1—C6—C50.8 (4)C13—C11—C12—C7177.9 (2)
N1—C1—C6—C5179.1 (2)N2—C7—C12—C11178.6 (2)
C4—C5—C6—C10.4 (4)C8—C7—C12—C110.2 (3)
N1—N2—C7—C12178.03 (19)C10—C9—C14—C16124.1 (2)
N1—N2—C7—C80.7 (3)C8—C9—C14—C1656.7 (3)
C12—C7—C8—O1177.7 (2)C10—C9—C14—C174.6 (3)
N2—C7—C8—O10.9 (3)C8—C9—C14—C17176.2 (2)
C12—C7—C8—C91.1 (3)C10—C9—C14—C15114.2 (2)
N2—C7—C8—C9179.8 (2)C8—C9—C14—C1565.0 (3)
O1—C8—C9—C10177.62 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.551 (2)145
C16—H16B···O10.962.302.958 (3)125
C15—H15C···O10.962.443.063 (3)123
C4—H4···Cg1i0.932.903.625 (3)136
Symmetry code: (i) x+1/2, y+1/2, z.
 

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