Literature DB >> 24109338

(E)-1-[(2,4,6-Tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.

Souheyla Chetioui1, Issam Boudraa, Sofiane Bouacida, Abdelkader Bouchoul, Salah Eddine Bouaoud.   

Abstract

The title azo mol-ecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intra-molecular O-H⋯N hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, mol-ecules are stacked in columns along the a axis by π-π inter-actions [centroid-centroid distances = 3.815 (3) and 3.990 (3) Å].

Entities:  

Year:  2013        PMID： 24109338      PMCID： PMC3793751          DOI： 10.1107/S1600536813018977

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


Related literature

For applications of azo compounds, see: Gale et al. (1998 ▶). For the synthesis of similar compounds, see: Wang et al. (2003 ▶); Heinrich et al. (2007 ▶). For bond lengths and angles in related azo compounds, see: Deveci et al. (2005 ▶); El-Ghamry et al. (2008 ▶).

Experimental

Crystal data

C16H9Br3N2O M = 484.98 Orthorhombic, a = 3.9904 (11) Å b = 15.689 (4) Å c = 24.580 (7) Å V = 1538.8 (7) Å3 Z = 4 Mo Kα radiation μ = 7.87 mm−1 T = 293 K 0.03 × 0.02 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.244, T max = 0.332 13143 measured reflections 3841 independent reflections 2910 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.066 S = 0.96 3841 reflections 199 parameters H-atom parameters constrained Δρmax = 0.44 e Å−3 Δρmin = −0.44 e Å−3 Absolute structure: Flack (1983 ▶), 1553 Friedel pairs Flack parameter: 0.004 (13) Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536813018977/is5290sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018977/is5290Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813018977/is5290Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H9Br3N2ODx = 2.093 Mg m−3
Mr = 484.98Melting point: 422 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2052 reflections
a = 3.9904 (11) Åθ = 3.1–28.6°
b = 15.689 (4) ŵ = 7.87 mm−1
c = 24.580 (7) ÅT = 293 K
V = 1538.8 (7) Å3Prism, red
Z = 40.03 × 0.02 × 0.02 mm
F(000) = 928
Bruker APEXII CCD diffractometer3841 independent reflections
Radiation source: fine-focus sealed tube2910 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −5→5
Tmin = 0.244, Tmax = 0.332k = −20→20
13143 measured reflectionsl = −32→32
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.066w = 1/[σ2(Fo2) + (0.0241P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
3841 reflectionsΔρmax = 0.44 e Å−3
199 parametersΔρmin = −0.44 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1553 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.004 (13)
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.
xyzUiso*/Ueq
Br1−0.12633 (11)−0.15833 (2)0.00161 (2)0.0379 (1)
Br20.51026 (12)0.09227 (3)0.12476 (2)0.0481 (2)
Br30.12463 (15)0.17248 (3)−0.08940 (2)0.0557 (2)
O1−0.4121 (9)0.02557 (17)−0.18018 (11)0.0512 (10)
N1−0.0964 (9)−0.01183 (18)−0.09266 (12)0.0352 (10)
N2−0.0368 (8)−0.08820 (18)−0.10973 (11)0.0317 (10)
C10.0433 (10)0.0081 (2)−0.04134 (14)0.0304 (11)
C20.0607 (9)−0.0479 (2)0.00323 (14)0.0304 (11)
C30.2004 (11)−0.0226 (2)0.05163 (14)0.0333 (12)
C40.3199 (11)0.0592 (2)0.05766 (15)0.0342 (11)
C50.2983 (11)0.1171 (2)0.01563 (15)0.0373 (14)
C60.1572 (11)0.0906 (2)−0.03316 (14)0.0337 (11)
C7−0.1725 (10)−0.1097 (2)−0.15902 (14)0.0307 (11)
C8−0.3485 (12)−0.0537 (3)−0.19353 (15)0.0387 (14)
C9−0.4639 (11)−0.0836 (3)−0.24475 (15)0.0432 (15)
C10−0.4111 (11)−0.1653 (3)−0.25976 (14)0.0437 (15)
C11−0.2321 (11)−0.2247 (3)−0.22725 (14)0.0355 (11)
C12−0.1079 (10)−0.1969 (2)−0.17622 (14)0.0299 (11)
C130.0637 (11)−0.2558 (2)−0.14376 (15)0.0360 (14)
C140.1125 (12)−0.3377 (2)−0.16128 (16)0.0443 (14)
C15−0.0059 (13)−0.3643 (3)−0.21170 (17)0.0487 (16)
C16−0.1756 (13)−0.3094 (3)−0.24383 (16)0.0470 (16)
H1−0.334560.03546−0.149930.0768*
H30.21435−0.060780.080450.0402*
H50.376330.172590.019850.0449*
H9−0.57652−0.04673−0.268070.0520*
H10−0.49596−0.18353−0.293010.0524*
H130.14544−0.23913−0.109960.0432*
H140.22647−0.37609−0.139160.0531*
H150.03174−0.41991−0.223310.0588*
H16−0.25621−0.32774−0.277340.0563*
U11U22U33U12U13U23
Br10.0446 (2)0.0286 (2)0.0405 (2)−0.0047 (2)0.0045 (2)0.0003 (2)
Br20.0505 (3)0.0582 (3)0.0356 (2)−0.0074 (2)−0.0023 (2)−0.0136 (2)
Br30.0867 (4)0.0324 (2)0.0481 (2)−0.0006 (3)0.0002 (3)0.0081 (2)
O10.072 (2)0.0408 (16)0.0409 (16)0.0086 (18)−0.0086 (17)0.0069 (13)
N10.045 (2)0.0281 (16)0.0324 (16)−0.0006 (16)0.0006 (17)−0.0034 (13)
N20.035 (2)0.0328 (16)0.0273 (14)−0.0046 (16)0.0039 (14)−0.0007 (13)
C10.031 (2)0.0277 (18)0.0324 (19)0.0023 (18)0.0052 (18)−0.0024 (15)
C20.031 (2)0.0263 (17)0.0339 (18)0.0023 (16)0.0058 (19)−0.0031 (16)
C30.036 (2)0.033 (2)0.031 (2)0.0011 (19)0.0048 (18)0.0007 (16)
C40.031 (2)0.041 (2)0.0306 (19)0.000 (2)0.0028 (19)−0.0106 (17)
C50.047 (3)0.028 (2)0.037 (2)−0.0053 (19)0.0080 (19)−0.0072 (16)
C60.042 (2)0.0272 (18)0.0318 (19)0.001 (2)0.0068 (19)0.0040 (16)
C70.033 (2)0.035 (2)0.0241 (18)−0.0030 (19)0.0019 (17)0.0007 (16)
C80.045 (3)0.036 (2)0.035 (2)−0.002 (2)0.001 (2)0.0053 (17)
C90.044 (3)0.056 (3)0.0297 (19)−0.002 (2)−0.005 (2)0.0108 (19)
C100.048 (3)0.059 (3)0.0240 (18)−0.013 (3)0.0018 (18)−0.0022 (19)
C110.037 (2)0.045 (2)0.0245 (19)−0.011 (2)0.0032 (18)−0.0023 (18)
C120.028 (2)0.0331 (19)0.0286 (18)−0.0085 (19)0.0068 (17)−0.0003 (15)
C130.040 (3)0.038 (2)0.0301 (19)−0.002 (2)0.0008 (18)−0.0044 (16)
C140.052 (3)0.036 (2)0.045 (2)0.005 (2)0.006 (2)−0.0030 (19)
C150.048 (3)0.041 (2)0.057 (3)−0.004 (2)0.013 (3)−0.015 (2)
C160.054 (3)0.053 (3)0.034 (2)−0.014 (2)0.006 (2)−0.016 (2)
Br1—C21.887 (3)C9—C101.350 (7)
Br2—C41.889 (4)C10—C111.420 (6)
Br3—C61.892 (3)C11—C161.408 (7)
O1—C81.311 (5)C11—C121.418 (5)
O1—H10.8200C12—C131.400 (5)
N1—N21.292 (4)C13—C141.369 (5)
N1—C11.414 (5)C14—C151.390 (6)
N2—C71.369 (5)C15—C161.351 (7)
C1—C21.406 (5)C3—H30.9300
C1—C61.387 (5)C5—H50.9300
C2—C31.373 (5)C9—H90.9300
C3—C41.377 (5)C10—H100.9300
C4—C51.378 (5)C13—H130.9300
C5—C61.389 (5)C14—H140.9300
C7—C81.409 (6)C15—H150.9300
C7—C121.455 (5)C16—H160.9300
C8—C91.420 (6)
C8—O1—H1109.00C12—C11—C16119.4 (4)
N2—N1—C1115.0 (3)C10—C11—C12118.2 (4)
N1—N2—C7116.3 (3)C7—C12—C13122.8 (3)
N1—C1—C2125.2 (3)C11—C12—C13118.2 (3)
C2—C1—C6117.0 (3)C7—C12—C11119.0 (3)
N1—C1—C6117.7 (3)C12—C13—C14120.7 (3)
Br1—C2—C3116.4 (2)C13—C14—C15120.9 (4)
C1—C2—C3121.0 (3)C14—C15—C16120.0 (4)
Br1—C2—C1122.5 (3)C11—C16—C15120.9 (4)
C2—C3—C4120.2 (3)C2—C3—H3120.00
Br2—C4—C5119.9 (3)C4—C3—H3120.00
C3—C4—C5120.8 (3)C4—C5—H5121.00
Br2—C4—C3119.3 (3)C6—C5—H5121.00
C4—C5—C6118.4 (3)C8—C9—H9120.00
Br3—C6—C5117.1 (2)C10—C9—H9120.00
C1—C6—C5122.5 (3)C9—C10—H10118.00
Br3—C6—C1120.4 (3)C11—C10—H10118.00
N2—C7—C12114.8 (3)C12—C13—H13120.00
C8—C7—C12120.0 (3)C14—C13—H13120.00
N2—C7—C8125.2 (3)C13—C14—H14120.00
O1—C8—C9118.2 (4)C15—C14—H14120.00
C7—C8—C9119.3 (4)C14—C15—H15120.00
O1—C8—C7122.5 (3)C16—C15—H15120.00
C8—C9—C10120.3 (4)C11—C16—H16120.00
C9—C10—C11123.2 (4)C15—C16—H16120.00
C10—C11—C16122.5 (4)
C1—N1—N2—C7179.2 (3)C12—C7—C8—O1−179.7 (4)
N2—N1—C1—C2−38.6 (5)C12—C7—C8—C90.6 (6)
N2—N1—C1—C6144.9 (4)N2—C7—C12—C11−178.7 (3)
N1—N2—C7—C84.8 (6)N2—C7—C12—C133.3 (6)
N1—N2—C7—C12−178.4 (3)C8—C7—C12—C11−1.6 (6)
N1—C1—C2—Br1−3.5 (5)C8—C7—C12—C13−179.6 (4)
N1—C1—C2—C3−179.8 (4)O1—C8—C9—C10−178.5 (4)
C6—C1—C2—Br1173.1 (3)C7—C8—C9—C101.3 (7)
C6—C1—C2—C3−3.2 (6)C8—C9—C10—C11−2.1 (7)
N1—C1—C6—Br3−0.1 (5)C9—C10—C11—C121.0 (6)
N1—C1—C6—C5179.9 (4)C9—C10—C11—C16−179.2 (4)
C2—C1—C6—Br3−176.9 (3)C10—C11—C12—C70.9 (6)
C2—C1—C6—C53.1 (6)C10—C11—C12—C13179.0 (4)
Br1—C2—C3—C4−175.1 (3)C16—C11—C12—C7−179.0 (4)
C1—C2—C3—C41.4 (6)C16—C11—C12—C13−0.9 (6)
C2—C3—C4—Br2179.9 (3)C10—C11—C16—C15−179.6 (4)
C2—C3—C4—C50.7 (6)C12—C11—C16—C150.2 (7)
Br2—C4—C5—C6179.9 (3)C7—C12—C13—C14178.7 (4)
C3—C4—C5—C6−0.8 (6)C11—C12—C13—C140.7 (6)
C4—C5—C6—Br3178.9 (3)C12—C13—C14—C150.2 (7)
C4—C5—C6—C1−1.1 (6)C13—C14—C15—C16−0.9 (7)
N2—C7—C8—O1−3.0 (7)C14—C15—C16—C110.7 (7)
N2—C7—C8—C9177.3 (4)
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.561 (4)144
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1⋯N10.821.852.561 (4)144
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