2-tert-Butyl-4-methyl-6-(phenyl­diazenyl)­phenol

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.

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

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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 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-tert-butyl-4-metyl-6-(phenyldiazenyl)phenol

Crystal data

C17H20N2O	F(000) = 576
Mr = 268.35	Dx = 1.204 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12915 reflections
a = 6.2333 (7) Å	θ = 2.2–31.8°
b = 10.4182 (12) Å	µ = 0.08 mm^−1
c = 22.788 (3) Å	T = 208 K
V = 1479.8 (3) Å^3	Prism, orange
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Bruker AXS SMART CCD diffractometer	1543 independent reflections
Radiation source: fine-focus sealed tube	1355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −7→7
Tmin = 0.985, Tmax = 0.985	k = −12→10
8784 measured reflections	l = −23→27

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 0.273P] where P = (Fo^2 + 2Fc^2)/3
1543 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.18 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
O1	0.1895 (3)	0.02999 (15)	0.20142 (7)	0.0379 (4)
H1	0.2884	0.0473	0.1791	0.057*
N1	0.4083 (3)	0.01523 (19)	0.10704 (8)	0.0313 (5)
N2	0.2864 (3)	−0.06981 (18)	0.08529 (8)	0.0306 (4)
C1	0.5837 (4)	0.0535 (2)	0.07062 (10)	0.0302 (5)
C2	0.6092 (4)	0.0120 (2)	0.01294 (10)	0.0373 (6)
H2	0.5088	−0.0426	−0.0041	0.045*
C3	0.7857 (4)	0.0528 (2)	−0.01870 (11)	0.0427 (6)
H3	0.8047	0.0252	−0.0572	0.051*
C4	0.9341 (4)	0.1344 (3)	0.00651 (12)	0.0427 (7)
H4	1.0523	0.1614	−0.0151	0.051*
C5	0.9083 (4)	0.1761 (3)	0.06334 (11)	0.0420 (6)
H5	1.0086	0.2310	0.0802	0.050*
C6	0.7321 (4)	0.1357 (2)	0.09535 (11)	0.0352 (6)
H6	0.7136	0.1641	0.1337	0.042*
C7	0.1107 (4)	−0.1087 (2)	0.12009 (10)	0.0285 (5)
C8	0.0638 (3)	−0.0609 (2)	0.17689 (10)	0.0274 (5)
C9	−0.1172 (4)	−0.1071 (2)	0.20728 (9)	0.0264 (5)
C10	−0.2438 (4)	−0.1969 (2)	0.17856 (10)	0.0301 (5)
H10	−0.3638	−0.2280	0.1982	0.036*
C11	−0.2030 (4)	−0.2438 (2)	0.12196 (10)	0.0320 (5)
C12	−0.0225 (4)	−0.1987 (2)	0.09399 (10)	0.0314 (5)
H12	0.0109	−0.2293	0.0568	0.038*
C13	−0.3528 (4)	−0.3379 (2)	0.09345 (11)	0.0404 (6)
H13A	−0.3003	−0.3593	0.0551	0.061*
H13B	−0.4929	−0.3003	0.0901	0.061*
H13C	−0.3611	−0.4143	0.1169	0.061*
C14	−0.1723 (4)	−0.0581 (2)	0.26954 (10)	0.0287 (5)
C15	−0.2292 (4)	0.0855 (2)	0.26698 (11)	0.0397 (6)
H15A	−0.2635	0.1155	0.3057	0.060*
H15B	−0.3507	0.0977	0.2417	0.060*
H15C	−0.1091	0.1328	0.2520	0.060*
C16	0.0164 (4)	−0.0798 (3)	0.31134 (10)	0.0419 (6)
H16A	−0.0206	−0.0489	0.3497	0.063*
H16B	0.1398	−0.0342	0.2972	0.063*
H16C	0.0483	−0.1698	0.3134	0.063*
C17	−0.3670 (4)	−0.1291 (2)	0.29479 (11)	0.0413 (6)
H17A	−0.3977	−0.0969	0.3334	0.062*
H17B	−0.3361	−0.2192	0.2970	0.062*
H17C	−0.4889	−0.1156	0.2698	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0353 (9)	0.0437 (9)	0.0348 (9)	−0.0140 (8)	0.0085 (8)	−0.0079 (7)
N1	0.0273 (10)	0.0362 (11)	0.0305 (10)	−0.0011 (9)	0.0039 (9)	0.0016 (8)
N2	0.0274 (9)	0.0319 (10)	0.0325 (10)	−0.0024 (9)	0.0024 (8)	0.0012 (8)
C1	0.0281 (11)	0.0325 (12)	0.0301 (12)	0.0030 (11)	0.0041 (10)	0.0046 (9)
C2	0.0363 (13)	0.0405 (13)	0.0352 (13)	−0.0007 (12)	0.0026 (11)	0.0007 (11)
C3	0.0452 (15)	0.0511 (15)	0.0317 (13)	0.0066 (15)	0.0116 (12)	0.0046 (11)
C4	0.0313 (13)	0.0499 (15)	0.0468 (16)	0.0033 (12)	0.0117 (12)	0.0187 (13)
C5	0.0349 (14)	0.0446 (15)	0.0465 (16)	−0.0073 (13)	0.0013 (12)	0.0104 (12)
C6	0.0357 (13)	0.0408 (13)	0.0292 (12)	0.0000 (12)	0.0022 (11)	0.0045 (10)
C7	0.0264 (11)	0.0292 (12)	0.0298 (12)	0.0020 (11)	0.0033 (10)	0.0033 (9)
C8	0.0255 (11)	0.0274 (11)	0.0292 (11)	0.0009 (10)	−0.0002 (9)	−0.0008 (9)
C9	0.0251 (11)	0.0265 (11)	0.0276 (11)	0.0031 (10)	0.0000 (10)	0.0038 (9)
C10	0.0258 (11)	0.0329 (11)	0.0315 (12)	−0.0010 (11)	0.0029 (10)	0.0032 (10)
C11	0.0333 (12)	0.0308 (12)	0.0318 (13)	−0.0017 (12)	−0.0034 (11)	0.0002 (9)
C12	0.0330 (12)	0.0338 (12)	0.0273 (12)	0.0013 (11)	0.0010 (10)	−0.0039 (10)
C13	0.0362 (14)	0.0434 (14)	0.0416 (14)	−0.0083 (12)	−0.0002 (12)	−0.0055 (12)
C14	0.0289 (11)	0.0308 (11)	0.0264 (11)	0.0009 (10)	0.0042 (10)	−0.0009 (9)
C15	0.0436 (14)	0.0379 (13)	0.0376 (14)	0.0027 (12)	0.0063 (12)	−0.0038 (11)
C16	0.0393 (14)	0.0584 (16)	0.0281 (12)	0.0071 (13)	0.0001 (11)	−0.0016 (12)
C17	0.0390 (14)	0.0472 (15)	0.0377 (14)	−0.0030 (12)	0.0137 (12)	−0.0034 (11)

Geometric parameters (Å, º)

O1—C8	1.350 (3)	C10—C11	1.403 (3)
O1—H1	0.82	C10—H10	0.93
N1—N2	1.268 (2)	C11—C12	1.376 (3)
N1—C1	1.429 (3)	C11—C13	1.502 (3)
N2—C7	1.411 (3)	C12—H12	0.93
C1—C6	1.381 (3)	C13—H13A	0.96
C1—C2	1.393 (3)	C13—H13B	0.96
C2—C3	1.383 (3)	C13—H13C	0.96
C2—H2	0.93	C14—C16	1.530 (3)
C3—C4	1.381 (4)	C14—C17	1.533 (3)
C3—H3	0.93	C14—C15	1.538 (3)
C4—C5	1.375 (4)	C15—H15A	0.96
C4—H4	0.93	C15—H15B	0.96
C5—C6	1.384 (3)	C15—H15C	0.96
C5—H5	0.93	C16—H16A	0.96
C6—H6	0.93	C16—H16B	0.96
C7—C12	1.387 (3)	C16—H16C	0.96
C7—C8	1.417 (3)	C17—H17A	0.96
C8—C9	1.409 (3)	C17—H17B	0.96
C9—C10	1.388 (3)	C17—H17C	0.96
C9—C14	1.546 (3)
C8—O1—H1	109.5	C10—C11—C13	120.8 (2)
N2—N1—C1	115.24 (19)	C11—C12—C7	121.5 (2)
N1—N2—C7	116.48 (19)	C11—C12—H12	119.3
C6—C1—C2	120.1 (2)	C7—C12—H12	119.3
C6—C1—N1	116.6 (2)	C11—C13—H13A	109.5
C2—C1—N1	123.3 (2)	C11—C13—H13B	109.5
C3—C2—C1	119.2 (2)	H13A—C13—H13B	109.5
C3—C2—H2	120.4	C11—C13—H13C	109.5
C1—C2—H2	120.4	H13A—C13—H13C	109.5
C4—C3—C2	120.4 (2)	H13B—C13—H13C	109.5
C4—C3—H3	119.8	C16—C14—C17	107.66 (19)
C2—C3—H3	119.8	C16—C14—C15	110.1 (2)
C5—C4—C3	120.5 (2)	C17—C14—C15	107.5 (2)
C5—C4—H4	119.7	C16—C14—C9	110.58 (18)
C3—C4—H4	119.7	C17—C14—C9	111.16 (19)
C4—C5—C6	119.6 (3)	C15—C14—C9	109.72 (18)
C4—C5—H5	120.2	C14—C15—H15A	109.5
C6—C5—H5	120.2	C14—C15—H15B	109.5
C1—C6—C5	120.3 (2)	H15A—C15—H15B	109.5
C1—C6—H6	119.8	C14—C15—H15C	109.5
C5—C6—H6	119.8	H15A—C15—H15C	109.5
C12—C7—N2	114.7 (2)	H15B—C15—H15C	109.5
C12—C7—C8	120.4 (2)	C14—C16—H16A	109.5
N2—C7—C8	124.9 (2)	C14—C16—H16B	109.5
O1—C8—C9	120.07 (19)	H16A—C16—H16B	109.5
O1—C8—C7	120.32 (19)	C14—C16—H16C	109.5
C9—C8—C7	119.6 (2)	H16A—C16—H16C	109.5
C10—C9—C8	117.0 (2)	H16B—C16—H16C	109.5
C10—C9—C14	121.9 (2)	C14—C17—H17A	109.5
C8—C9—C14	121.1 (2)	C14—C17—H17B	109.5
C9—C10—C11	124.5 (2)	H17A—C17—H17B	109.5
C9—C10—H10	117.8	C14—C17—H17C	109.5
C11—C10—H10	117.8	H17A—C17—H17C	109.5
C12—C11—C10	117.1 (2)	H17B—C17—H17C	109.5
C12—C11—C13	122.1 (2)
C1—N1—N2—C7	−179.46 (19)	C7—C8—C9—C10	−1.3 (3)
N2—N1—C1—C6	−173.4 (2)	O1—C8—C9—C14	−1.7 (3)
N2—N1—C1—C2	6.6 (3)	C7—C8—C9—C14	179.46 (19)
C6—C1—C2—C3	0.8 (4)	C8—C9—C10—C11	0.1 (3)
N1—C1—C2—C3	−179.1 (2)	C14—C9—C10—C11	179.3 (2)
C1—C2—C3—C4	−0.4 (4)	C9—C10—C11—C12	1.3 (3)
C2—C3—C4—C5	0.0 (4)	C9—C10—C11—C13	−178.0 (2)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12—C7	−1.4 (3)
C2—C1—C6—C5	−0.8 (4)	C13—C11—C12—C7	177.9 (2)
N1—C1—C6—C5	179.1 (2)	N2—C7—C12—C11	−178.6 (2)
C4—C5—C6—C1	0.4 (4)	C8—C7—C12—C11	0.2 (3)
N1—N2—C7—C12	178.03 (19)	C10—C9—C14—C16	124.1 (2)
N1—N2—C7—C8	−0.7 (3)	C8—C9—C14—C16	−56.7 (3)
C12—C7—C8—O1	−177.7 (2)	C10—C9—C14—C17	4.6 (3)
N2—C7—C8—O1	0.9 (3)	C8—C9—C14—C17	−176.2 (2)
C12—C7—C8—C9	1.1 (3)	C10—C9—C14—C15	−114.2 (2)
N2—C7—C8—C9	179.8 (2)	C8—C9—C14—C15	65.0 (3)
O1—C8—C9—C10	177.62 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.551 (2)	145
C16—H16B···O1	0.96	2.30	2.958 (3)	125
C15—H15C···O1	0.96	2.44	3.063 (3)	123
C4—H4···Cg1^i	0.93	2.90	3.625 (3)	136

Symmetry code: (i) x+1/2, −y+1/2, −z.