1-[(E)-2-(5-tert-Butyl-2-hy-droxy-phen-yl)diazen-1-yl]naphthalen-2-ol.

The non-H atoms of the title compound, C20H20N2O2, is located on a mirror plane except two methyl groups of the tert-butyl group. Intra-molecular N-H⋯O hydrogen bonds exist between the hy-droxy and diazenyl groups. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into supra-molecular chains running along the a-axis direction.

Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▶). For related azo compounds, see: Yazıcı et al. (2010 ▶); Karadayı et al. (2006 ▶); Oakes (2002 ▶); Olivieri et al. (1989 ▶). For the synthesis, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C20H20N2O2

M = 320.38

Monoclinic,

a = 9.696 (5) Å

b = 6.606 (5) Å

c = 13.385 (5) Å

β = 110.249 (5)°

V = 804.3 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.55 × 0.22 × 0.11 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.978, T max = 0.991

8889 measured reflections

2642 independent reflections

1767 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.144

S = 0.89

2642 reflections

142 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814001731/xu5764sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001731/xu5764Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001731/xu5764Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H20N2O2	F(000) = 340
Mr = 320.38	Dx = 1.323 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 2015 reflections
a = 9.696 (5) Å	θ = 3.2–30.4°
b = 6.606 (5) Å	µ = 0.09 mm−1
c = 13.385 (5) Å	T = 293 K
β = 110.249 (5)°	Prism, red
V = 804.3 (8) Å3	0.55 × 0.22 × 0.11 mm
Z = 2

Bruker APEXII diffractometer	2642 independent reflections
Radiation source: fine-focus sealed tube	1767 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
CCD rotation images, thin slices scans	θmax = 30.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −13→13
Tmin = 0.978, Tmax = 0.991	k = −7→9
8889 measured reflections	l = −18→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.0766P)2 + 0.359P] where P = (Fo2 + 2Fc2)/3
2642 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.43 e Å−3
12 restraints	Δρmin = −0.23 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
O1	0.77215 (13)	0.75000	0.56321 (10)	0.0270 (4)
O2	0.31274 (13)	0.75000	0.19510 (10)	0.0277 (4)
N1	0.48377 (15)	0.75000	0.39638 (11)	0.0180 (4)
N2	0.60014 (15)	0.75000	0.37081 (11)	0.0194 (4)
C1	0.50711 (18)	0.75000	0.50553 (13)	0.0164 (4)
C2	0.64717 (17)	0.75000	0.58490 (14)	0.0195 (4)
C3	0.66094 (19)	0.75000	0.69373 (14)	0.0242 (5)
C4	0.53890 (19)	0.75000	0.72205 (14)	0.0240 (5)
C5	0.39521 (18)	0.75000	0.64529 (14)	0.0191 (5)
C6	0.37768 (17)	0.75000	0.53520 (13)	0.0172 (4)
C7	0.23305 (19)	0.75000	0.46054 (15)	0.0258 (5)
C8	0.1138 (2)	0.75000	0.49354 (16)	0.0326 (6)
C9	0.1312 (2)	0.75000	0.60179 (16)	0.0300 (6)
C10	0.2695 (2)	0.75000	0.67614 (15)	0.0246 (5)
C11	0.57989 (18)	0.75000	0.26191 (13)	0.0190 (4)
C12	0.44281 (18)	0.75000	0.17815 (14)	0.0209 (5)
C13	0.44203 (19)	0.75000	0.07401 (14)	0.0259 (5)
C14	0.5727 (2)	0.75000	0.05311 (14)	0.0254 (5)
C15	0.71035 (18)	0.75000	0.13444 (13)	0.0195 (5)
C16	0.70929 (18)	0.75000	0.23809 (14)	0.0203 (5)
C17	0.85759 (19)	0.75000	0.11508 (14)	0.0220 (5)
C18	0.94634 (15)	0.5609 (2)	0.16604 (12)	0.0300 (4)
C19	0.8368 (2)	0.75000	−0.00394 (16)	0.0327 (6)
H1	0.75270	0.75000	0.49850	0.0410*
H2	0.32790	0.75000	0.25930	0.0420*
H3	0.75380	0.75000	0.74610	0.0290*
H4	0.55030	0.75000	0.79390	0.0290*
H7	0.21840	0.75000	0.38810	0.0310*
H8	0.01970	0.75000	0.44290	0.0390*
H9	0.04930	0.75000	0.62290	0.0360*
H10	0.28130	0.75000	0.74810	0.0300*
H13	0.35290	0.75000	0.01770	0.0310*
H14	0.56850	0.75000	−0.01730	0.0310*
H16	0.79880	0.75000	0.29410	0.0240*
H18A	0.89250	0.44160	0.13420	0.0360*
H18B	0.96370	0.56020	0.24120	0.0360*
H18C	1.03870	0.56280	0.15450	0.0360*
H19A	0.78450	0.63120	−0.03610	0.0390*
H19B	0.93110	0.75000	−0.01250	0.0390*

	U11	U22	U33	U12	U13	U23
O1	0.0180 (6)	0.0410 (8)	0.0236 (6)	0.0000	0.0091 (5)	0.0000
O2	0.0191 (6)	0.0418 (8)	0.0233 (6)	0.0000	0.0088 (5)	0.0000
N1	0.0201 (6)	0.0172 (7)	0.0188 (7)	0.0000	0.0096 (5)	0.0000
N2	0.0208 (6)	0.0220 (7)	0.0178 (7)	0.0000	0.0096 (5)	0.0000
C1	0.0192 (7)	0.0150 (7)	0.0162 (7)	0.0000	0.0078 (6)	0.0000
C2	0.0174 (7)	0.0202 (8)	0.0219 (8)	0.0000	0.0082 (6)	0.0000
C3	0.0207 (8)	0.0303 (10)	0.0193 (8)	0.0000	0.0040 (6)	0.0000
C4	0.0272 (8)	0.0282 (10)	0.0169 (8)	0.0000	0.0080 (7)	0.0000
C5	0.0224 (8)	0.0173 (8)	0.0198 (8)	0.0000	0.0100 (6)	0.0000
C6	0.0201 (7)	0.0146 (8)	0.0185 (8)	0.0000	0.0086 (6)	0.0000
C7	0.0208 (8)	0.0371 (11)	0.0194 (8)	0.0000	0.0070 (7)	0.0000
C8	0.0188 (8)	0.0494 (13)	0.0298 (10)	0.0000	0.0085 (7)	0.0000
C9	0.0238 (8)	0.0384 (11)	0.0331 (10)	0.0000	0.0165 (8)	0.0000
C10	0.0298 (9)	0.0260 (9)	0.0232 (9)	0.0000	0.0159 (7)	0.0000
C11	0.0212 (7)	0.0197 (8)	0.0177 (8)	0.0000	0.0087 (6)	0.0000
C12	0.0191 (7)	0.0217 (9)	0.0233 (8)	0.0000	0.0093 (6)	0.0000
C13	0.0213 (8)	0.0357 (11)	0.0187 (8)	0.0000	0.0044 (6)	0.0000
C14	0.0296 (9)	0.0324 (10)	0.0160 (8)	0.0000	0.0102 (7)	0.0000
C15	0.0232 (8)	0.0183 (8)	0.0204 (8)	0.0000	0.0117 (7)	0.0000
C16	0.0196 (7)	0.0238 (9)	0.0193 (8)	0.0000	0.0089 (6)	0.0000
C17	0.0248 (8)	0.0242 (9)	0.0218 (8)	0.0000	0.0142 (7)	0.0000
C18	0.0306 (6)	0.0293 (7)	0.0356 (7)	0.0053 (6)	0.0185 (5)	0.0029 (6)
C19	0.0347 (10)	0.0448 (13)	0.0256 (9)	0.0000	0.0194 (8)	0.0000

O1—C2	1.340 (2)	C14—C15	1.400 (3)
O2—C12	1.357 (3)	C15—C17	1.537 (3)
O1—H1	0.8200	C15—C16	1.391 (3)
O2—H2	0.8200	C17—C18i	1.536 (2)
N1—C1	1.399 (2)	C17—C18	1.536 (2)
N1—N2	1.288 (2)	C17—C19	1.535 (3)
N2—C11	1.402 (2)	C3—H3	0.9300
C1—C6	1.441 (3)	C4—H4	0.9300
C1—C2	1.405 (3)	C7—H7	0.9300
C2—C3	1.416 (3)	C8—H8	0.9300
C3—C4	1.362 (3)	C9—H9	0.9300
C4—C5	1.416 (3)	C10—H10	0.9300
C5—C6	1.424 (3)	C13—H13	0.9300
C5—C10	1.416 (3)	C14—H14	0.9300
C6—C7	1.413 (3)	C16—H16	0.9300
C7—C8	1.373 (3)	C18—H18A	0.9600
C8—C9	1.400 (3)	C18—H18B	0.9600
C9—C10	1.366 (3)	C18—H18C	0.9600
C11—C12	1.411 (3)	C19—H19A	0.9500
C11—C16	1.397 (3)	C19—H19B	0.9600
C12—C13	1.391 (3)	C19—H19Ai	0.9500
C13—C14	1.389 (3)
O1···N1	2.913 (3)	C11···C4iii	3.529 (3)
O1···N2	2.538 (3)	C11···C4iv	3.529 (3)
O1···C9ii	3.338 (4)	C11···C4v	3.529 (3)
O1···C7iii	3.317 (3)	C11···C5iv	3.508 (3)
O1···C7iv	3.317 (3)	C11···C5v	3.508 (3)
O1···C7v	3.317 (3)	C11···C10iv	3.591 (3)
O1···C7vi	3.317 (3)	C11···C10v	3.591 (3)
O1···C9vii	3.338 (4)	C11···C5vi	3.508 (3)
O2···N1	2.630 (3)	C11···C4vi	3.529 (3)
O2···N2	2.960 (3)	C11···C5iii	3.508 (3)
O1···H9vii	2.5200	C11···C10iii	3.591 (3)
O1···H9ii	2.5200	C11···C10vi	3.591 (3)
O2···H18Cviii	2.8100	C12···C4iii	3.544 (3)
O2···H18Cix	2.8100	C12···C4iv	3.544 (3)
N1···O1	2.913 (3)	C12···C4v	3.544 (3)
N1···O2	2.630 (3)	C12···C4vi	3.544 (3)
N2···C5iv	3.311 (3)	C16···C10iii	3.480 (3)
N2···C5v	3.311 (3)	C16···C10iv	3.480 (3)
N2···C5iii	3.311 (3)	C16···C10v	3.480 (3)
N2···O1	2.538 (3)	C16···C10vi	3.480 (3)
N2···O2	2.960 (3)	C11···H1	3.0300
N2···C5vi	3.311 (3)	C14···H19Ai	2.8200
N1···H2	1.9300	C14···H19A	2.8200
N1···H7	2.5400	C16···H18B	2.7500
N1···H1	2.4900	C16···H18Bi	2.7500
N2···H1	1.8300	C18···H16	2.8700
N2···H2	2.5400	C19···H14	2.5500
C1···C1iv	3.307 (3)	H1···N1	2.4900
C1···C1v	3.307 (3)	H1···N2	1.8300
C1···C6iv	3.588 (3)	H1···C11	3.0300
C1···C6v	3.588 (3)	H2···N1	1.9300
C1···C1iii	3.307 (3)	H2···N2	2.5400
C1···C1vi	3.307 (3)	H2···H7	2.3200
C1···C6iii	3.588 (3)	H4···H10	2.4600
C1···C6vi	3.588 (3)	H4···H14x	2.4700
C4···C11iv	3.529 (3)	H4···H14xi	2.4700
C4···C11v	3.529 (3)	H7···N1	2.5400
C4···C12iv	3.544 (3)	H7···H2	2.3200
C4···C12v	3.544 (3)	H8···H16viii	2.3700
C4···C11iii	3.529 (3)	H8···H16ix	2.3700
C4···C11vi	3.529 (3)	H9···O1viii	2.5200
C4···C12iii	3.544 (3)	H9···O1ix	2.5200
C4···C12vi	3.544 (3)	H10···H4	2.4600
C5···N2iv	3.311 (3)	H14···C19	2.5500
C5···N2v	3.311 (3)	H14···H4xii	2.4700
C5···C11iv	3.508 (3)	H14···H19A	2.3300
C5···C11v	3.508 (3)	H14···H4xiii	2.4700
C5···N2iii	3.311 (3)	H14···H19Ai	2.3300
C5···N2vi	3.311 (3)	H16···C18	2.8700
C5···C11iii	3.508 (3)	H16···H8ii	2.3700
C5···C11vi	3.508 (3)	H16···H18B	2.3300
C6···C1iv	3.588 (3)	H16···C18i	2.8700
C6···C1v	3.588 (3)	H16···H8vii	2.3700
C6···C1iii	3.588 (3)	H16···H18Bi	2.3300
C6···C1vi	3.588 (3)	H18A···H19A	2.4900
C7···O1iv	3.317 (3)	H18A···H18Axiv	2.5300
C7···O1v	3.317 (3)	H18B···C16	2.7500
C7···O1iii	3.317 (3)	H18B···H16	2.3300
C7···O1vi	3.317 (3)	H18B···H18Bi	2.5100
C9···O1viii	3.338 (4)	H18C···O2ii	2.8100
C9···O1ix	3.338 (4)	H18C···H19B	2.4500
C10···C11iv	3.591 (3)	H18C···O2vii	2.8100
C10···C11v	3.591 (3)	H18C···H18Ci	2.4700
C10···C16iv	3.480 (3)	H19A···C14	2.8200
C10···C16v	3.480 (3)	H19A···H14	2.3300
C10···C11iii	3.591 (3)	H19A···H18A	2.4900
C10···C11vi	3.591 (3)	H19B···H18C	2.4500
C10···C16iii	3.480 (3)	H19B···H18Ci	2.4500
C10···C16vi	3.480 (3)
C2—O1—H1	110.00	C15—C17—C18i	109.60 (10)
C12—O2—H2	110.00	C18—C17—C18i	108.81 (14)
N2—N1—C1	115.96 (14)	C18i—C17—C19	108.24 (11)
N1—N2—C11	117.14 (14)	C18—C17—C19	108.24 (11)
N1—C1—C6	116.50 (15)	C15—C17—C18	109.60 (10)
N1—C1—C2	123.67 (16)	C2—C3—H3	120.00
C2—C1—C6	119.84 (15)	C4—C3—H3	120.00
O1—C2—C3	116.90 (16)	C3—C4—H4	119.00
O1—C2—C1	123.09 (16)	C5—C4—H4	119.00
C1—C2—C3	120.01 (16)	C6—C7—H7	120.00
C2—C3—C4	120.31 (17)	C8—C7—H7	120.00
C3—C4—C5	121.97 (16)	C7—C8—H8	119.00
C4—C5—C10	121.23 (16)	C9—C8—H8	119.00
C6—C5—C10	119.70 (16)	C8—C9—H9	120.00
C4—C5—C6	119.07 (16)	C10—C9—H9	120.00
C5—C6—C7	117.77 (16)	C5—C10—H10	119.00
C1—C6—C5	118.80 (15)	C9—C10—H10	120.00
C1—C6—C7	123.43 (15)	C12—C13—H13	120.00
C6—C7—C8	120.85 (17)	C14—C13—H13	120.00
C7—C8—C9	121.32 (19)	C13—C14—H14	119.00
C8—C9—C10	119.38 (19)	C15—C14—H14	119.00
C5—C10—C9	120.99 (18)	C11—C16—H16	119.00
C12—C11—C16	119.46 (16)	C15—C16—H16	118.00
N2—C11—C12	125.48 (16)	C17—C18—H18A	110.00
N2—C11—C16	115.06 (15)	C17—C18—H18B	110.00
C11—C12—C13	118.22 (17)	C17—C18—H18C	109.00
O2—C12—C13	118.99 (16)	H18A—C18—H18B	109.00
O2—C12—C11	122.79 (16)	H18A—C18—H18C	109.00
C12—C13—C14	120.85 (17)	H18B—C18—H18C	109.00
C13—C14—C15	122.27 (16)	C17—C19—H19A	109.00
C16—C15—C17	119.75 (15)	C17—C19—H19B	110.00
C14—C15—C16	116.19 (17)	C17—C19—H19Ai	109.00
C14—C15—C17	124.06 (15)	H19A—C19—H19B	109.00
C11—C16—C15	123.01 (16)	H19A—C19—H19Ai	111.00
C15—C17—C19	112.28 (15)	H19Ai—C19—H19B	109.00
C1—N1—N2—C11	180.00 (1)	C6—C5—C10—C9	0.00 (1)
N2—N1—C1—C2	0.00 (1)	C1—C6—C7—C8	180.00 (1)
N2—N1—C1—C6	180.00 (1)	C5—C6—C7—C8	0.00 (1)
N1—N2—C11—C12	0.00 (1)	C6—C7—C8—C9	0.00 (1)
N1—N2—C11—C16	180.00 (1)	C7—C8—C9—C10	0.00 (1)
N1—C1—C2—O1	0.00 (1)	C8—C9—C10—C5	0.00 (1)
N1—C1—C2—C3	180.00 (1)	N2—C11—C12—O2	0.00 (1)
C6—C1—C2—O1	180.00 (1)	N2—C11—C12—C13	180.00 (1)
C6—C1—C2—C3	0.00 (1)	C16—C11—C12—O2	180.00 (1)
N1—C1—C6—C5	180.00 (1)	C16—C11—C12—C13	0.00 (1)
N1—C1—C6—C7	0.00 (1)	N2—C11—C16—C15	180.00 (1)
C2—C1—C6—C5	0.00 (1)	C12—C11—C16—C15	0.00 (1)
C2—C1—C6—C7	180.00 (1)	O2—C12—C13—C14	180.00 (1)
O1—C2—C3—C4	180.00 (1)	C11—C12—C13—C14	0.00 (1)
C1—C2—C3—C4	0.00 (1)	C12—C13—C14—C15	0.00 (1)
C2—C3—C4—C5	0.00 (1)	C13—C14—C15—C16	0.00 (1)
C3—C4—C5—C6	0.00 (1)	C13—C14—C15—C17	180.00 (1)
C3—C4—C5—C10	180.00 (1)	C14—C15—C16—C11	0.00 (1)
C4—C5—C6—C1	0.00 (1)	C17—C15—C16—C11	180.00 (1)
C4—C5—C6—C7	180.00 (1)	C14—C15—C17—C18	−120.32 (10)
C10—C5—C6—C1	180.00 (1)	C14—C15—C17—C19	0.00 (1)
C10—C5—C6—C7	0.00 (1)	C16—C15—C17—C18	59.68 (10)
C4—C5—C10—C9	180.00 (1)	C16—C15—C17—C19	180.00 (1)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.83	2.538 (3)	143
O2—H2···N1	0.82	1.93	2.630 (3)	142
C9—H9···O1viii	0.93	2.52	3.338 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.83	2.538 (3)	143
O2—H2⋯N1	0.82	1.93	2.630 (3)	142
C9—H9⋯O1i	0.93	2.52	3.338 (4)	146

Symmetry code: (i) .