2-[(E)-(5-tert-Butyl-2-hydroxy-phen-yl)-diazen-yl]benzoic acid.

The title compound, C(17)H(18)N(2)O(3), is approximately planar, owing in part to an intra-molecular bifurcated O-H⋯(N,O) hydrogen bond; the dihedral angle between the two aromatic rings is 23.86 (9)°. In the crystal struture, centrosymmetrically related mol-ecules associate into dimers via the eight-membered carboxyl-ate {⋯H-O-C=O}(2) synthon.

Related literature

For a related structure, see: Basu Baul et al. (2007 ▶). For background, see: Willem et al. (1998 ▶). For reviews of organotin carboxyl­ates, see: Tiekink (1991 ▶).

Experimental

Crystal data

C17H18N2O3

M = 298.33

Monoclinic,

a = 5.9052 (19) Å

b = 10.872 (4) Å

c = 23.126 (8) Å

β = 94.432 (4)°

V = 1480.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 98 (2) K

0.35 × 0.16 × 0.08 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: none

8445 measured reflections

3068 independent reflections

2610 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.144

S = 1.12

3068 reflections

205 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku Americas Corporation, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803290X/ng2500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803290X/ng2500Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H18N2O3	F(000) = 632
Mr = 298.33	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7951 reflections
a = 5.9052 (19) Å	θ = 2.1–40.6°
b = 10.872 (4) Å	µ = 0.09 mm−1
c = 23.126 (8) Å	T = 98 K
β = 94.432 (4)°	Prism, red
V = 1480.3 (9) Å3	0.35 × 0.16 × 0.08 mm
Z = 4

Rigaku Saturn724 (2x2 bin mode) diffractometer	2610 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.065
graphite	θmax = 26.5°, θmin = 2.6°
Detector resolution: 28.5714 pixels mm-1	h = −7→7
dtprofit.ref scans	k = −13→10
8445 measured reflections	l = −28→27
3068 independent reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.6036P] where P = (Fo2 + 2Fc2)/3
3068 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.8680 (2)	0.51703 (14)	0.43659 (6)	0.0263 (3)
O2	0.7565 (3)	0.39227 (16)	0.50557 (6)	0.0321 (4)
H2O	0.8640	0.4274	0.5250	0.048*
O3	1.0671 (2)	0.59362 (14)	0.33194 (6)	0.0246 (3)
H3O	0.9599	0.5542	0.3451	0.037*
N1	0.7361 (2)	0.43713 (16)	0.32732 (6)	0.0190 (3)
N2	0.7593 (2)	0.40523 (16)	0.27524 (6)	0.0191 (4)
C1	0.5577 (3)	0.37647 (19)	0.41419 (8)	0.0201 (4)
C2	0.5548 (3)	0.37664 (18)	0.35309 (8)	0.0185 (4)
C3	0.3792 (3)	0.31732 (19)	0.32013 (8)	0.0199 (4)
H3	0.3774	0.3177	0.2790	0.024*
C4	0.2083 (3)	0.25820 (19)	0.34670 (8)	0.0218 (4)
H4	0.0892	0.2186	0.3238	0.026*
C5	0.2102 (3)	0.2566 (2)	0.40711 (8)	0.0243 (4)
H5	0.0928	0.2157	0.4254	0.029*
C6	0.3842 (3)	0.3148 (2)	0.44028 (8)	0.0237 (4)
H6	0.3857	0.3128	0.4814	0.028*
C7	0.7425 (3)	0.43611 (19)	0.45205 (7)	0.0204 (4)
C8	0.9426 (3)	0.46168 (18)	0.25033 (7)	0.0179 (4)
C9	1.0885 (3)	0.55091 (18)	0.27794 (7)	0.0188 (4)
C10	1.2692 (3)	0.59442 (19)	0.24792 (8)	0.0226 (4)
H10	1.3672	0.6559	0.2650	0.027*
C11	1.3068 (3)	0.54898 (19)	0.19368 (8)	0.0218 (4)
H11	1.4315	0.5800	0.1745	0.026*
C12	1.1679 (3)	0.45878 (19)	0.16583 (8)	0.0195 (4)
C13	0.9861 (3)	0.41778 (19)	0.19516 (7)	0.0201 (4)
H13	0.8872	0.3577	0.1772	0.024*
C14	1.2258 (3)	0.4010 (2)	0.10821 (8)	0.0221 (4)
C15	1.3827 (3)	0.2902 (2)	0.12276 (9)	0.0285 (5)
H15A	1.4224	0.2510	0.0867	0.043*
H15B	1.3040	0.2306	0.1459	0.043*
H15C	1.5213	0.3183	0.1449	0.043*
C16	1.3498 (4)	0.4929 (2)	0.07107 (9)	0.0350 (5)
H16A	1.3845	0.4533	0.0347	0.052*
H16B	1.4913	0.5194	0.0924	0.052*
H16C	1.2524	0.5646	0.0624	0.052*
C17	1.0117 (3)	0.3565 (2)	0.07259 (8)	0.0300 (5)
H17A	1.0544	0.3198	0.0363	0.045*
H17B	0.9099	0.4263	0.0639	0.045*
H17C	0.9341	0.2948	0.0948	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0322 (7)	0.0266 (8)	0.0198 (6)	−0.0063 (6)	−0.0008 (5)	0.0028 (6)
O2	0.0389 (8)	0.0371 (10)	0.0193 (7)	−0.0135 (7)	−0.0048 (6)	0.0059 (6)
O3	0.0284 (7)	0.0242 (8)	0.0218 (6)	−0.0050 (6)	0.0052 (5)	−0.0054 (6)
N1	0.0187 (7)	0.0213 (9)	0.0171 (7)	0.0019 (6)	0.0024 (5)	0.0007 (6)
N2	0.0185 (7)	0.0208 (9)	0.0181 (7)	0.0017 (6)	0.0029 (6)	0.0004 (6)
C1	0.0215 (9)	0.0184 (10)	0.0208 (9)	0.0024 (7)	0.0033 (7)	−0.0002 (7)
C2	0.0187 (8)	0.0165 (9)	0.0207 (8)	0.0032 (7)	0.0045 (6)	0.0008 (7)
C3	0.0208 (8)	0.0192 (10)	0.0200 (8)	0.0044 (7)	0.0031 (7)	−0.0011 (7)
C4	0.0182 (8)	0.0196 (10)	0.0274 (9)	0.0014 (7)	0.0009 (7)	−0.0014 (8)
C5	0.0222 (9)	0.0263 (11)	0.0252 (9)	−0.0010 (8)	0.0067 (7)	0.0047 (8)
C6	0.0283 (9)	0.0244 (11)	0.0185 (8)	0.0016 (8)	0.0034 (7)	0.0005 (8)
C7	0.0240 (9)	0.0210 (10)	0.0166 (8)	0.0024 (8)	0.0041 (7)	0.0001 (7)
C8	0.0173 (8)	0.0188 (10)	0.0177 (8)	0.0006 (7)	0.0021 (6)	0.0011 (7)
C9	0.0217 (8)	0.0152 (9)	0.0194 (8)	0.0016 (7)	0.0010 (6)	−0.0010 (7)
C10	0.0240 (9)	0.0184 (10)	0.0254 (9)	−0.0033 (7)	0.0018 (7)	0.0003 (8)
C11	0.0203 (8)	0.0201 (10)	0.0256 (9)	−0.0014 (7)	0.0050 (7)	0.0043 (8)
C12	0.0200 (8)	0.0187 (10)	0.0199 (8)	0.0019 (7)	0.0025 (6)	0.0021 (7)
C13	0.0198 (8)	0.0215 (10)	0.0189 (8)	−0.0016 (7)	0.0006 (7)	−0.0011 (7)
C14	0.0212 (9)	0.0260 (11)	0.0197 (9)	−0.0016 (8)	0.0060 (7)	0.0003 (8)
C15	0.0262 (9)	0.0303 (12)	0.0292 (10)	0.0024 (8)	0.0040 (8)	−0.0069 (9)
C16	0.0397 (12)	0.0378 (14)	0.0295 (10)	−0.0080 (10)	0.0157 (9)	0.0012 (10)
C17	0.0250 (9)	0.0468 (15)	0.0185 (9)	0.0007 (9)	0.0039 (7)	−0.0049 (9)

O1—C7	1.221 (2)	C9—C10	1.400 (3)
O2—C7	1.323 (2)	C10—C11	1.382 (3)
O2—H2O	0.84	C10—H10	0.9500
O3—C9	1.348 (2)	C11—C12	1.403 (3)
O3—H3O	0.84	C11—H11	0.9500
N1—N2	1.271 (2)	C12—C13	1.387 (2)
N1—C2	1.426 (2)	C12—C14	1.536 (3)
N2—C8	1.406 (2)	C13—H13	0.9500
C1—C6	1.400 (3)	C14—C17	1.533 (3)
C1—C2	1.412 (2)	C14—C16	1.539 (3)
C1—C7	1.494 (3)	C14—C15	1.541 (3)
C2—C3	1.396 (3)	C15—H15A	0.9800
C3—C4	1.380 (3)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.396 (3)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.387 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C8—C13	1.404 (2)	C17—H17C	0.9800
C8—C9	1.417 (3)
C7—O2—H2O	109.0	C10—C11—C12	122.50 (17)
C9—O3—H3O	106.6	C10—C11—H11	118.7
N2—N1—C2	114.19 (16)	C12—C11—H11	118.7
N1—N2—C8	114.34 (15)	C13—C12—C11	116.58 (17)
C6—C1—C2	118.67 (17)	C13—C12—C14	121.71 (17)
C6—C1—C7	118.77 (16)	C11—C12—C14	121.52 (16)
C2—C1—C7	122.54 (16)	C12—C13—C8	122.54 (17)
C3—C2—C1	119.78 (17)	C12—C13—H13	118.7
C3—C2—N1	122.33 (16)	C8—C13—H13	118.7
C1—C2—N1	117.88 (16)	C17—C14—C12	111.46 (15)
C4—C3—C2	120.65 (17)	C17—C14—C16	108.24 (17)
C4—C3—H3	119.7	C12—C14—C16	111.47 (17)
C2—C3—H3	119.7	C17—C14—C15	109.10 (18)
C3—C4—C5	120.12 (17)	C12—C14—C15	107.52 (15)
C3—C4—H4	119.9	C16—C14—C15	109.01 (17)
C5—C4—H4	119.9	C14—C15—H15A	109.5
C6—C5—C4	119.72 (18)	C14—C15—H15B	109.5
C6—C5—H5	120.1	H15A—C15—H15B	109.5
C4—C5—H5	120.1	C14—C15—H15C	109.5
C5—C6—C1	121.06 (17)	H15A—C15—H15C	109.5
C5—C6—H6	119.5	H15B—C15—H15C	109.5
C1—C6—H6	119.5	C14—C16—H16A	109.5
O1—C7—O2	122.55 (17)	C14—C16—H16B	109.5
O1—C7—C1	124.99 (16)	H16A—C16—H16B	109.5
O2—C7—C1	112.46 (17)	C14—C16—H16C	109.5
C13—C8—N2	115.13 (16)	H16A—C16—H16C	109.5
C13—C8—C9	119.64 (16)	H16B—C16—H16C	109.5
N2—C8—C9	125.11 (16)	C14—C17—H17A	109.5
O3—C9—C10	118.24 (17)	C14—C17—H17B	109.5
O3—C9—C8	123.79 (16)	H17A—C17—H17B	109.5
C10—C9—C8	117.94 (17)	C14—C17—H17C	109.5
C11—C10—C9	120.77 (18)	H17A—C17—H17C	109.5
C11—C10—H10	119.6	H17B—C17—H17C	109.5
C9—C10—H10	119.6
C2—N1—N2—C8	−178.01 (15)	C13—C8—C9—O3	−176.45 (17)
C6—C1—C2—C3	0.8 (3)	N2—C8—C9—O3	−0.7 (3)
C7—C1—C2—C3	178.85 (18)	C13—C8—C9—C10	1.6 (3)
C6—C1—C2—N1	−178.37 (17)	N2—C8—C9—C10	177.41 (17)
C7—C1—C2—N1	−0.4 (3)	O3—C9—C10—C11	176.50 (17)
N2—N1—C2—C3	−18.1 (3)	C8—C9—C10—C11	−1.7 (3)
N2—N1—C2—C1	161.07 (17)	C9—C10—C11—C12	0.4 (3)
C1—C2—C3—C4	−0.1 (3)	C10—C11—C12—C13	1.0 (3)
N1—C2—C3—C4	179.05 (17)	C10—C11—C12—C14	−174.16 (18)
C2—C3—C4—C5	−0.4 (3)	C11—C12—C13—C8	−1.0 (3)
C3—C4—C5—C6	0.1 (3)	C14—C12—C13—C8	174.10 (17)
C4—C5—C6—C1	0.6 (3)	N2—C8—C13—C12	−176.47 (17)
C2—C1—C6—C5	−1.1 (3)	C9—C8—C13—C12	−0.3 (3)
C7—C1—C6—C5	−179.17 (18)	C13—C12—C14—C17	32.4 (3)
C6—C1—C7—O1	−160.29 (19)	C11—C12—C14—C17	−152.69 (19)
C2—C1—C7—O1	21.7 (3)	C13—C12—C14—C16	153.50 (18)
C6—C1—C7—O2	19.2 (3)	C11—C12—C14—C16	−31.6 (3)
C2—C1—C7—O2	−158.82 (18)	C13—C12—C14—C15	−87.1 (2)
N1—N2—C8—C13	173.37 (16)	C11—C12—C14—C15	87.8 (2)
N1—N2—C8—C9	−2.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N1	0.84	1.86	2.587 (2)	144
O3—H3O···O1	0.84	2.26	2.894 (2)	132
O2—H2O···O1i	0.84	1.86	2.687 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯N1	0.84	1.86	2.587 (2)	144
O3—H3O⋯O1	0.84	2.26	2.894 (2)	132
O2—H2O⋯O1i	0.84	1.86	2.687 (2)	170

Symmetry code: (i) .