Literature DB >> 23125741

4-{(E)-2-[4-(But-3-en-1-yl-oxy)phen-yl]diazen-1-yl}benzoic acid.

Md Lutfor Rahman¹, Huey Chong Kwong, Mashitah Mohd Yusoff, Gurumurthy Hegde, Mohamed Ibrahim Mohamed Tahir, Mohamad Zaki Ab Rahman.

Abstract

The title compound, C(17)H(16)N(2)O(3), has an E conformation about the azobenzene (-N=N-) linkage. The benzene rings are twisted slightly with respect to each other [6.79 (9)°], while the dihedral angle between the plane through the carb-oxy group and the attached benzene ring is 3.2 (2)°. In the crystal, mol-ecules are oriented with the carb-oxy groups head-to-head, forming O-H⋯O hydrogen-bonded inversion dimers. These dimers are connected by C-H⋯O hydrogen-bonds into layers lying parallel to the (013) plane.

Entities: Chemical Disease Gene

Year: 2012 PMID： 23125741 PMCID： PMC3470328 DOI： 10.1107/S1600536812038718

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the physical properties of compounds containing an azobenzene (–N=N–) linkage, see: Chigrinov (2005 ▶); Hegde (2007 ▶). For related structures, see: Yu & Liu (2009 ▶); Lai et al. (2002 ▶); Centore & Tuzi (2003 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16N2O3 M = 296.33 Triclinic, a = 7.0937 (7) Å b = 9.8687 (10) Å c = 11.2490 (11) Å α = 87.334 (8)° β = 73.475 (8)° γ = 75.174 (8)° V = 729.54 (13) Å3 Z = 2 Cu Kα radiation μ = 0.77 mm−1 T = 100 K 0.26 × 0.16 × 0.04 mm

Data collection

Oxford Diffraction Gemini diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.85, T max = 0.97 9940 measured reflections 2783 independent reflections 2298 reflections with I > 2.0σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.146 S = 1.00 2773 reflections 199 parameters H-atom parameters constrained Δρmax = 0.51 e Å−3 Δρmin = −0.33 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: CRYSTALS. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038718/su2476sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038718/su2476Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812038718/su2476Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₆N₂O₃	Z = 2
M_r = 296.33	F(000) = 312
Triclinic, P1	D_x = 1.349 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 7.0937 (7) Å	Cell parameters from 3768 reflections
b = 9.8687 (10) Å	θ = 4–71°
c = 11.2490 (11) Å	µ = 0.77 mm⁻¹
α = 87.334 (8)°	T = 100 K
β = 73.475 (8)°	Plate, brown
γ = 75.174 (8)°	0.26 × 0.16 × 0.04 mm
V = 729.54 (13) Å³

Oxford Diffraction Gemini diffractometer	2783 independent reflections
Radiation source: sealed x-ray tube	2298 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 71.5°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −8→8
T_min = 0.85, T_max = 0.97	k = −11→11
9940 measured reflections	l = −13→13

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.146	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.06P)² + 0.76P], where P = (max(F_o²,0) + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.0003776
2773 reflections	Δρ_max = 0.51 e Å⁻³
199 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

Refinement. This compound, 9940 numbers of reflections were collected and measured during the refinement. Symmetry related reflections were measured more than once and after merging the symmetry equivalent reflections there were only 2783 reflection left. 10 more reflections were filtered, as sigma cutoff was set as 3 and (sinθ/x)set to>0.01 (to eliminate reflection measured near the vicinity of beam stop) therefore numbers of reflection reduced to 2773.

	x	y	z	U_iso*/U_eq
O1	0.0122 (2)	1.34005 (15)	0.07329 (14)	0.0276
C2	0.1938 (3)	1.3516 (2)	0.04699 (18)	0.0221
O3	0.2517 (2)	1.45464 (14)	−0.00910 (14)	0.0281
C4	0.3484 (3)	1.2387 (2)	0.08338 (17)	0.0215
C5	0.2990 (3)	1.1180 (2)	0.14000 (18)	0.0231
C6	0.4449 (3)	1.0125 (2)	0.17190 (18)	0.0233
C7	0.6447 (3)	1.0260 (2)	0.14525 (18)	0.0220
N8	0.8099 (2)	0.92608 (18)	0.17206 (15)	0.0238
N9	0.7751 (2)	0.81065 (17)	0.21222 (15)	0.0235
C10	0.9450 (3)	0.7184 (2)	0.24132 (18)	0.0243
C11	1.1313 (3)	0.7536 (2)	0.2247 (2)	0.0293
C12	1.2896 (3)	0.6624 (2)	0.2565 (2)	0.0321
C13	1.2665 (3)	0.5349 (2)	0.30679 (19)	0.0302
O14	1.4341 (2)	0.45519 (16)	0.33669 (15)	0.0364
C15	1.4290 (4)	0.3232 (2)	0.3930 (2)	0.0349
C16	1.6307 (4)	0.2701 (3)	0.4247 (2)	0.0399
C17	1.6430 (4)	0.1366 (3)	0.4911 (2)	0.0388
C18	1.7890 (4)	0.0213 (3)	0.4581 (3)	0.0455
C19	1.0850 (3)	0.4962 (2)	0.32338 (19)	0.0310
C20	0.9240 (3)	0.5897 (2)	0.28909 (19)	0.0287
C21	0.6931 (3)	1.1467 (2)	0.09065 (19)	0.0252
C22	0.5462 (3)	1.2529 (2)	0.06039 (18)	0.0238
H51	0.1631	1.1098	0.1566	0.0298*
H61	0.4112	0.9298	0.2120	0.0302*
H111	1.1483	0.8433	0.1888	0.0379*
H121	1.4168	0.6860	0.2448	0.0406*
H151	1.3110	0.3369	0.4683	0.0453*
H152	1.4146	0.2584	0.3328	0.0447*
H161	1.6418	0.3468	0.4751	0.0512*
H162	1.7478	0.2531	0.3482	0.0518*
H171	1.5325	0.1356	0.5657	0.0520*
H182	1.9017	0.0237	0.3829	0.0605*
H181	1.7859	−0.0632	0.5068	0.0604*
H191	1.0658	0.4083	0.3577	0.0394*
H201	0.8003	0.5652	0.2975	0.0369*
H211	0.8278	1.1552	0.0740	0.0331*
H221	0.5794	1.3355	0.0213	0.0322*
H2	0.1704	1.5151	−0.0423	0.0500*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0212 (7)	0.0239 (8)	0.0399 (8)	−0.0047 (6)	−0.0132 (6)	0.0029 (6)
C2	0.0228 (10)	0.0191 (10)	0.0252 (10)	−0.0034 (8)	−0.0092 (8)	−0.0018 (8)
O3	0.0270 (8)	0.0210 (8)	0.0385 (8)	−0.0048 (6)	−0.0154 (6)	0.0082 (6)
C4	0.0213 (10)	0.0195 (10)	0.0243 (9)	−0.0033 (8)	−0.0087 (8)	−0.0015 (8)
C5	0.0183 (9)	0.0230 (11)	0.0295 (10)	−0.0048 (8)	−0.0094 (8)	0.0016 (8)
C6	0.0236 (10)	0.0203 (10)	0.0279 (10)	−0.0064 (8)	−0.0098 (8)	0.0030 (8)
C7	0.0213 (10)	0.0198 (10)	0.0248 (10)	−0.0009 (8)	−0.0100 (8)	−0.0005 (8)
N8	0.0217 (8)	0.0225 (9)	0.0272 (9)	−0.0028 (7)	−0.0094 (7)	0.0016 (7)
N9	0.0207 (8)	0.0218 (9)	0.0258 (8)	−0.0003 (7)	−0.0073 (7)	−0.0008 (7)
C10	0.0235 (10)	0.0231 (11)	0.0228 (10)	0.0018 (8)	−0.0079 (8)	−0.0014 (8)
C11	0.0256 (11)	0.0273 (11)	0.0338 (11)	−0.0009 (9)	−0.0116 (9)	−0.0001 (9)
C12	0.0260 (11)	0.0317 (12)	0.0391 (12)	−0.0018 (9)	−0.0145 (9)	−0.0008 (10)
C13	0.0281 (11)	0.0311 (12)	0.0276 (10)	0.0047 (9)	−0.0119 (9)	−0.0046 (9)
O14	0.0356 (9)	0.0287 (8)	0.0461 (9)	0.0007 (7)	−0.0216 (7)	0.0028 (7)
C15	0.0410 (13)	0.0270 (12)	0.0348 (12)	−0.0002 (10)	−0.0149 (10)	−0.0006 (9)
C16	0.0456 (14)	0.0359 (14)	0.0420 (13)	−0.0055 (11)	−0.0228 (11)	0.0019 (10)
C17	0.0383 (13)	0.0374 (13)	0.0408 (13)	−0.0019 (10)	−0.0187 (10)	0.0032 (10)
C18	0.0463 (15)	0.0372 (14)	0.0563 (16)	−0.0033 (11)	−0.0264 (13)	0.0022 (12)
C19	0.0390 (12)	0.0218 (11)	0.0273 (10)	0.0000 (9)	−0.0086 (9)	0.0013 (8)
C20	0.0272 (11)	0.0270 (11)	0.0284 (11)	−0.0022 (9)	−0.0064 (8)	−0.0009 (8)
C21	0.0196 (9)	0.0265 (11)	0.0310 (10)	−0.0066 (8)	−0.0087 (8)	0.0002 (8)
C22	0.0237 (10)	0.0196 (10)	0.0294 (10)	−0.0055 (8)	−0.0101 (8)	0.0031 (8)

O1—C2	1.271 (2)	C13—O14	1.367 (3)
C2—O3	1.268 (2)	C13—C19	1.395 (3)
C2—C4	1.483 (3)	O14—C15	1.426 (3)
O3—H2	0.868	C15—C16	1.529 (3)
C4—C5	1.401 (3)	C15—H151	0.993
C4—C22	1.395 (3)	C15—H152	0.996
C5—C6	1.382 (3)	C16—C17	1.479 (3)
C5—H51	0.952	C16—H161	0.998
C6—C7	1.403 (3)	C16—H162	0.997
C6—H61	0.965	C17—C18	1.312 (4)
C7—N8	1.421 (3)	C17—H171	0.974
C7—C21	1.391 (3)	C18—H182	0.989
N8—N9	1.263 (2)	C18—H181	0.978
N9—C10	1.423 (3)	C19—C20	1.408 (3)
C10—C11	1.411 (3)	C19—H191	0.959
C10—C20	1.382 (3)	C20—H201	0.947
C11—C12	1.371 (3)	C21—C22	1.382 (3)
C11—H111	0.977	C21—H211	0.945
C12—C13	1.384 (3)	C22—H221	0.959
C12—H121	0.960

O1—C2—O3	123.76 (18)	O14—C15—C16	106.04 (19)
O1—C2—C4	118.68 (17)	O14—C15—H151	109.0
O3—C2—C4	117.56 (17)	C16—C15—H151	111.8
C2—O3—H2	119.6	O14—C15—H152	108.8
C2—C4—C5	121.02 (17)	C16—C15—H152	111.3
C2—C4—C22	119.37 (17)	H151—C15—H152	109.7
C5—C4—C22	119.61 (18)	C15—C16—C17	112.4 (2)
C4—C5—C6	120.55 (18)	C15—C16—H161	106.1
C4—C5—H51	119.1	C17—C16—H161	112.0
C6—C5—H51	120.4	C15—C16—H162	111.1
C5—C6—C7	119.42 (18)	C17—C16—H162	107.0
C5—C6—H61	120.9	H161—C16—H162	108.3
C7—C6—H61	119.7	C16—C17—C18	125.6 (3)
C6—C7—N8	125.56 (18)	C16—C17—H171	116.3
C6—C7—C21	119.98 (18)	C18—C17—H171	118.0
N8—C7—C21	114.44 (17)	C17—C18—H182	117.5
C7—N8—N9	115.89 (16)	C17—C18—H181	120.8
N8—N9—C10	112.56 (16)	H182—C18—H181	121.7
N9—C10—C11	122.76 (18)	C13—C19—C20	118.9 (2)
N9—C10—C20	118.03 (18)	C13—C19—H191	122.3
C11—C10—C20	119.21 (19)	C20—C19—H191	118.8
C10—C11—C12	120.7 (2)	C19—C20—C10	120.4 (2)
C10—C11—H111	119.5	C19—C20—H201	120.6
C12—C11—H111	119.8	C10—C20—H201	118.9
C11—C12—C13	119.9 (2)	C7—C21—C22	120.46 (18)
C11—C12—H121	120.8	C7—C21—H211	119.3
C13—C12—H121	119.3	C22—C21—H211	120.3
C12—C13—O14	114.02 (19)	C4—C22—C21	119.94 (18)
C12—C13—C19	120.84 (19)	C4—C22—H221	119.3
O14—C13—C19	125.1 (2)	C21—C22—H221	120.7
C13—O14—C15	119.93 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H2···O1ⁱ	0.87	1.76	2.612 (3)	166 (1)
C21—H211···O1ⁱⁱ	0.95	2.50	3.275 (3)	139 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H2⋯O1ⁱ	0.87	1.76	2.612 (3)	166 (1)
C21—H211⋯O1ⁱⁱ	0.95	2.50	3.275 (3)	139 (1)

Symmetry codes: (i) ; (ii) .

1 in total

1. 4,4'-azinodibenzoic Acid.

Authors: Qun-Di Yu; Yun-Yu Liu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-05

1 in total