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

The title benzene hemisolvate, C(17)H(18)N(2)O(3)·0.5C(6)H(6), features an essentially planar (the r.m.s. deviation of the non-H atoms, excluding methyl-C, is 0.071 Å) diazo mol-ecule with an E conformation about the N=N bond, and a half-mol-ecule of benzene disposed about a centre of inversion. The dihedral angle formed between the benzene rings of the diazo mol-ecule is 7.69 (12)°. In the crystal, centrosymmetrically related dimers associate via the eight-membered carboxylic acid dimer synthon, {⋯HOC(=O)}(2), and these are connected into a supra-molecular chain along the b axis via C-H⋯O contacts.

Related literature

For background to and motivation for the synthesis of the title compound, see: Basu Baul et al. (2010a ▶,b ▶,c ▶). For the structure of a related diazo compound, see: Basu Baul et al. (2008 ▶).

Experimental

Crystal data

C17H18N2O3·0.5C6H6

M = 337.39

Triclinic,

a = 6.0960 (2) Å

b = 7.3578 (3) Å

c = 20.6562 (7) Å

α = 81.326 (2)°

β = 88.992 (2)°

γ = 71.355 (2)°

V = 867.37 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.49 × 0.09 × 0.03 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.859, T max = 1

11445 measured reflections

3053 independent reflections

1888 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.157

S = 1.08

3053 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003880/hg2642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003880/hg2642Isup2.hkl

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

C17H18N2O3·0.5C6H6	Z = 2
Mr = 337.39	F(000) = 358
Triclinic, P1	Dx = 1.292 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0960 (2) Å	Cell parameters from 2230 reflections
b = 7.3578 (3) Å	θ = 3.0–25.1°
c = 20.6562 (7) Å	µ = 0.09 mm−1
α = 81.326 (2)°	T = 100 K
β = 88.992 (2)°	Plate, orange
γ = 71.355 (2)°	0.49 × 0.09 × 0.03 mm
V = 867.37 (5) Å3

Bruker SMART APEXII diffractometer	3053 independent reflections
Radiation source: sealed tube	1888 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 25.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.859, Tmax = 1	k = −8→8
11445 measured reflections	l = −24→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0458P] where P = (Fo2 + 2Fc2)/3
3053 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.9406 (3)	0.7864 (2)	0.00097 (8)	0.0270 (5)
O2	0.7757 (3)	1.0387 (2)	0.05359 (8)	0.0270 (5)
H2O	0.8709	1.0827	0.0321	0.040*
O3	0.0159 (3)	0.2070 (2)	0.17405 (9)	0.0295 (5)
H3O	0.1019	0.2690	0.1569	0.044*
N1	0.1696 (3)	0.4998 (3)	0.15671 (9)	0.0214 (5)
N2	0.0282 (3)	0.5895 (3)	0.19601 (9)	0.0214 (5)
C1	0.7939 (4)	0.8718 (4)	0.03965 (11)	0.0200 (6)
C2	0.6296 (4)	0.7767 (3)	0.07027 (11)	0.0186 (6)
C3	0.6505 (4)	0.5880 (4)	0.06190 (11)	0.0215 (6)
H3	0.7704	0.5196	0.0362	0.026*
C4	0.4971 (4)	0.5002 (4)	0.09100 (11)	0.0224 (6)
H4	0.5120	0.3709	0.0856	0.027*
C5	0.3208 (4)	0.6011 (4)	0.12827 (11)	0.0187 (6)
C6	0.2955 (4)	0.7910 (4)	0.13581 (11)	0.0210 (6)
H6	0.1722	0.8610	0.1602	0.025*
C7	0.4513 (4)	0.8766 (4)	0.10745 (11)	0.0224 (6)
H7	0.4371	1.0055	0.1133	0.027*
C8	−0.1216 (4)	0.4932 (4)	0.22568 (11)	0.0193 (6)
C9	−0.1262 (4)	0.3104 (4)	0.21544 (12)	0.0215 (6)
C10	−0.2869 (4)	0.2363 (4)	0.24863 (12)	0.0254 (6)
H10	−0.2942	0.1134	0.2419	0.030*
C11	−0.4361 (4)	0.3394 (4)	0.29125 (12)	0.0245 (6)
H11	−0.5437	0.2849	0.3134	0.029*
C12	−0.4341 (4)	0.5213 (4)	0.30302 (11)	0.0201 (6)
C13	−0.2753 (4)	0.5933 (4)	0.26916 (12)	0.0213 (6)
H13	−0.2699	0.7169	0.2757	0.026*
C14	−0.5974 (4)	0.6396 (4)	0.35012 (12)	0.0241 (6)
C15	−0.7522 (5)	0.5308 (4)	0.38459 (13)	0.0357 (8)
H15A	−0.8514	0.5080	0.3520	0.053*
H15B	−0.8489	0.6083	0.4154	0.053*
H15C	−0.6557	0.4060	0.4085	0.053*
C16	−0.4527 (5)	0.6816 (4)	0.40241 (13)	0.0344 (7)
H16A	−0.3585	0.5590	0.4281	0.052*
H16B	−0.5559	0.7619	0.4314	0.052*
H16C	−0.3511	0.7508	0.3811	0.052*
C17	−0.7517 (5)	0.8319 (4)	0.31170 (13)	0.0307 (7)
H17A	−0.6543	0.9044	0.2899	0.046*
H17B	−0.8531	0.9088	0.3419	0.046*
H17C	−0.8462	0.8052	0.2787	0.046*
C18	0.8298 (5)	0.0370 (4)	0.45204 (13)	0.0313 (7)
H18	0.7123	0.0620	0.4192	0.038*
C19	0.9784 (5)	0.1460 (4)	0.44705 (13)	0.0305 (7)
H19	0.9640	0.2458	0.4108	0.037*
C20	1.1478 (5)	0.1084 (4)	0.49518 (13)	0.0334 (7)
H20	1.2501	0.1831	0.4920	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0223 (10)	0.0252 (10)	0.0326 (10)	−0.0054 (8)	0.0128 (8)	−0.0077 (8)
O2	0.0259 (11)	0.0235 (11)	0.0361 (11)	−0.0136 (9)	0.0103 (9)	−0.0074 (9)
O3	0.0302 (11)	0.0227 (10)	0.0384 (11)	−0.0097 (9)	0.0153 (9)	−0.0123 (9)
N1	0.0173 (11)	0.0237 (12)	0.0241 (11)	−0.0065 (10)	0.0041 (9)	−0.0067 (10)
N2	0.0183 (11)	0.0236 (12)	0.0235 (11)	−0.0074 (10)	0.0046 (9)	−0.0062 (10)
C1	0.0195 (14)	0.0191 (14)	0.0220 (14)	−0.0065 (12)	0.0018 (11)	−0.0045 (11)
C2	0.0167 (14)	0.0205 (14)	0.0185 (13)	−0.0058 (11)	0.0021 (11)	−0.0038 (11)
C3	0.0192 (14)	0.0264 (16)	0.0190 (13)	−0.0059 (12)	0.0056 (11)	−0.0071 (11)
C4	0.0219 (14)	0.0221 (15)	0.0251 (14)	−0.0075 (12)	0.0046 (11)	−0.0087 (11)
C5	0.0154 (13)	0.0229 (15)	0.0198 (13)	−0.0082 (11)	0.0025 (11)	−0.0046 (11)
C6	0.0179 (14)	0.0221 (15)	0.0224 (13)	−0.0039 (12)	0.0072 (11)	−0.0080 (11)
C7	0.0228 (15)	0.0224 (15)	0.0232 (14)	−0.0079 (12)	0.0029 (12)	−0.0060 (12)
C8	0.0175 (13)	0.0217 (14)	0.0208 (13)	−0.0094 (12)	0.0004 (11)	−0.0032 (11)
C9	0.0194 (14)	0.0222 (15)	0.0226 (14)	−0.0054 (12)	0.0022 (11)	−0.0051 (11)
C10	0.0265 (15)	0.0208 (15)	0.0316 (15)	−0.0109 (13)	0.0044 (12)	−0.0059 (12)
C11	0.0212 (15)	0.0279 (16)	0.0260 (14)	−0.0118 (12)	0.0032 (12)	−0.0012 (12)
C12	0.0168 (13)	0.0231 (15)	0.0196 (13)	−0.0054 (11)	0.0013 (11)	−0.0027 (11)
C13	0.0201 (14)	0.0218 (14)	0.0245 (14)	−0.0079 (12)	0.0023 (11)	−0.0088 (11)
C14	0.0204 (14)	0.0304 (16)	0.0239 (14)	−0.0096 (12)	0.0056 (11)	−0.0085 (12)
C15	0.0292 (16)	0.0411 (18)	0.0372 (17)	−0.0118 (14)	0.0160 (14)	−0.0081 (14)
C16	0.0270 (16)	0.0456 (19)	0.0325 (16)	−0.0092 (14)	0.0073 (13)	−0.0177 (14)
C17	0.0257 (16)	0.0315 (17)	0.0335 (16)	−0.0048 (13)	0.0096 (13)	−0.0111 (13)
C18	0.0308 (17)	0.0334 (17)	0.0301 (16)	−0.0093 (14)	0.0007 (13)	−0.0084 (13)
C19	0.0381 (17)	0.0265 (16)	0.0270 (15)	−0.0099 (14)	0.0067 (13)	−0.0055 (12)
C20	0.0365 (18)	0.0378 (18)	0.0335 (16)	−0.0199 (15)	0.0076 (14)	−0.0114 (14)

O1—C1	1.265 (3)	C11—C12	1.400 (4)
O2—C1	1.274 (3)	C11—H11	0.9500
O2—H2O	0.8400	C12—C13	1.379 (3)
O3—C9	1.345 (3)	C12—C14	1.537 (3)
O3—H3O	0.8400	C13—H13	0.9500
N1—N2	1.269 (3)	C14—C15	1.526 (3)
N1—C5	1.427 (3)	C14—C16	1.533 (4)
N2—C8	1.406 (3)	C14—C17	1.534 (4)
C1—C2	1.478 (3)	C15—H15A	0.9800
C2—C3	1.390 (3)	C15—H15B	0.9800
C2—C7	1.393 (3)	C15—H15C	0.9800
C3—C4	1.379 (3)	C16—H16A	0.9800
C3—H3	0.9500	C16—H16B	0.9800
C4—C5	1.390 (3)	C16—H16C	0.9800
C4—H4	0.9500	C17—H17A	0.9800
C5—C6	1.389 (3)	C17—H17B	0.9800
C6—C7	1.376 (3)	C17—H17C	0.9800
C6—H6	0.9500	C18—C20i	1.383 (4)
C7—H7	0.9500	C18—C19	1.383 (4)
C8—C13	1.398 (3)	C18—H18	0.9500
C8—C9	1.401 (3)	C19—C20	1.379 (4)
C9—C10	1.390 (3)	C19—H19	0.9500
C10—C11	1.382 (3)	C20—C18i	1.383 (4)
C10—H10	0.9500	C20—H20	0.9500
C1—O2—H2O	109.5	C13—C12—C14	120.3 (2)
C9—O3—H3O	109.5	C11—C12—C14	123.6 (2)
N2—N1—C5	114.0 (2)	C12—C13—C8	123.2 (2)
N1—N2—C8	115.6 (2)	C12—C13—H13	118.4
O1—C1—O2	123.8 (2)	C8—C13—H13	118.4
O1—C1—C2	119.2 (2)	C15—C14—C16	108.3 (2)
O2—C1—C2	117.0 (2)	C15—C14—C17	108.6 (2)
C3—C2—C7	119.5 (2)	C16—C14—C17	109.4 (2)
C3—C2—C1	120.4 (2)	C15—C14—C12	111.9 (2)
C7—C2—C1	120.1 (2)	C16—C14—C12	109.1 (2)
C4—C3—C2	120.0 (2)	C17—C14—C12	109.44 (19)
C4—C3—H3	120.0	C14—C15—H15A	109.5
C2—C3—H3	120.0	C14—C15—H15B	109.5
C3—C4—C5	119.9 (2)	H15A—C15—H15B	109.5
C3—C4—H4	120.0	C14—C15—H15C	109.5
C5—C4—H4	120.0	H15A—C15—H15C	109.5
C6—C5—C4	120.5 (2)	H15B—C15—H15C	109.5
C6—C5—N1	123.0 (2)	C14—C16—H16A	109.5
C4—C5—N1	116.4 (2)	C14—C16—H16B	109.5
C7—C6—C5	119.2 (2)	H16A—C16—H16B	109.5
C7—C6—H6	120.4	C14—C16—H16C	109.5
C5—C6—H6	120.4	H16A—C16—H16C	109.5
C6—C7—C2	120.8 (2)	H16B—C16—H16C	109.5
C6—C7—H7	119.6	C14—C17—H17A	109.5
C2—C7—H7	119.6	C14—C17—H17B	109.5
C13—C8—C9	119.4 (2)	H17A—C17—H17B	109.5
C13—C8—N2	114.9 (2)	C14—C17—H17C	109.5
C9—C8—N2	125.7 (2)	H17A—C17—H17C	109.5
O3—C9—C10	119.3 (2)	H17B—C17—H17C	109.5
O3—C9—C8	122.4 (2)	C20i—C18—C19	120.0 (3)
C10—C9—C8	118.3 (2)	C20i—C18—H18	120.0
C11—C10—C9	120.7 (2)	C19—C18—H18	120.0
C11—C10—H10	119.6	C20—C19—C18	119.3 (3)
C9—C10—H10	119.6	C20—C19—H19	120.3
C10—C11—C12	122.3 (2)	C18—C19—H19	120.3
C10—C11—H11	118.8	C19—C20—C18i	120.7 (3)
C12—C11—H11	118.8	C19—C20—H20	119.7
C13—C12—C11	116.1 (2)	C18i—C20—H20	119.7
C5—N1—N2—C8	−179.2 (2)	N2—C8—C9—O3	−0.9 (4)
O1—C1—C2—C3	6.4 (4)	C13—C8—C9—C10	0.8 (4)
O2—C1—C2—C3	−174.6 (2)	N2—C8—C9—C10	−179.7 (2)
O1—C1—C2—C7	−173.2 (2)	O3—C9—C10—C11	−179.7 (2)
O2—C1—C2—C7	5.8 (4)	C8—C9—C10—C11	−0.8 (4)
C7—C2—C3—C4	−0.8 (4)	C9—C10—C11—C12	0.2 (4)
C1—C2—C3—C4	179.6 (2)	C10—C11—C12—C13	0.5 (4)
C2—C3—C4—C5	0.5 (4)	C10—C11—C12—C14	−179.9 (2)
C3—C4—C5—C6	0.9 (4)	C11—C12—C13—C8	−0.5 (4)
C3—C4—C5—N1	−180.0 (2)	C14—C12—C13—C8	179.9 (2)
N2—N1—C5—C6	−8.3 (3)	C9—C8—C13—C12	−0.1 (4)
N2—N1—C5—C4	172.6 (2)	N2—C8—C13—C12	−179.7 (2)
C4—C5—C6—C7	−1.8 (4)	C13—C12—C14—C15	−177.7 (2)
N1—C5—C6—C7	179.1 (2)	C11—C12—C14—C15	2.7 (4)
C5—C6—C7—C2	1.5 (4)	C13—C12—C14—C16	−57.8 (3)
C3—C2—C7—C6	−0.2 (4)	C11—C12—C14—C16	122.6 (3)
C1—C2—C7—C6	179.4 (2)	C13—C12—C14—C17	61.9 (3)
N1—N2—C8—C13	179.6 (2)	C11—C12—C14—C17	−117.7 (3)
N1—N2—C8—C9	0.1 (4)	C20i—C18—C19—C20	−0.2 (4)
C13—C8—C9—O3	179.6 (2)	C18—C19—C20—C18i	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1	0.84	1.87	2.587 (3)	142
O2—H2o···O1ii	0.84	1.79	2.614 (3)	167
C3—H3···O1iii	0.95	2.59	3.473 (3)	155
C6—H6···O3iv	0.95	2.48	3.201 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯N1	0.84	1.87	2.587 (3)	142
O2—H2o⋯O1i	0.84	1.79	2.614 (3)	167
C3—H3⋯O1ii	0.95	2.59	3.473 (3)	155
C6—H6⋯O3iii	0.95	2.48	3.201 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) .