Literature DB >> 22064802

6-Hy-droxy-2H-1,3-benzodioxole-5-carbaldehyde.

Mehbub I K Momin, Neil Koorbanally, Deresh Ramjugernath, Muhammad D Bala.   

Abstract

The title compound, C(8)H(6)O(4), crystallizes with two independent mol-ecules in the asymmetric unit. The benzodioxole ring system is almost planar in each mol-ecule, with maximum deviations of 0.008 (1) and 0.007 (1) Å. The mol-ecular structure is characterized by strong electrostatic intra-molecular O⋯O contacts [2.649 (3) Å] and intra-molecular O-H⋯O hydrogen-bonding inter-actions. Inter-molecular O⋯O inter-actions [3.001 (2) Å] are observed in the crystal structure.

Entities:  

Year:  2011        PMID： 22064802      PMCID： PMC3201492          DOI： 10.1107/S1600536811037019

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


Related literature

For the preparation, see: Juhász et al. (2007 ▶); Akselsen et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). The title compound is a starting material and an inter­mediate in the synthesis of biologically active compounds. These compounds have shown HIV-1 integrase inhibitory activity (Bailly et al., 2005 ▶), dopamine D1 receptor full agonist (Cueva, et al. 2006 ▶) and glycogen phospho­rylase inhibitory activity (Juhász et al., 2007 ▶).

Experimental

Crystal data

C8H6O4 M = 166.13 Monoclinic, a = 6.4916 (3) Å b = 12.8242 (7) Å c = 16.7122 (8) Å β = 96.258 (3)° V = 1382.99 (12) Å3 Z = 8 Mo Kα radiation μ = 0.13 mm−1 T = 173 K 0.38 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer 10746 measured reflections 2708 independent reflections 1348 reflections with I > 2σ(I) R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.125 S = 0.94 2708 reflections 219 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.31 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037019/qm2028sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037019/qm2028Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811037019/qm2028Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C8H6O4F(000) = 688
Mr = 166.13Dx = 1.596 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1671 reflections
a = 6.4916 (3) Åθ = 2.5–26.6°
b = 12.8242 (7) ŵ = 0.13 mm−1
c = 16.7122 (8) ÅT = 173 K
β = 96.258 (3)°Needle, colourless
V = 1382.99 (12) Å30.38 × 0.11 × 0.10 mm
Z = 8
Bruker APEXII CCD diffractometer1348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.081
graphiteθmax = 26.0°, θmin = 2.0°
φ and ω scansh = −7→8
10746 measured reflectionsk = −15→15
2708 independent reflectionsl = −18→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 0.94w = 1/[σ2(Fo2) + (0.0556P)2] where P = (Fo2 + 2Fc2)/3
2708 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −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.
xyzUiso*/Ueq
C10.0179 (4)0.62547 (19)0.46651 (15)0.0211 (6)
C20.2306 (4)0.6144 (2)0.49173 (15)0.0221 (6)
C30.3046 (4)0.6148 (2)0.57346 (15)0.0272 (7)
H30.44740.60590.59150.033*
C40.1604 (4)0.6288 (2)0.62576 (14)0.0233 (6)
C5−0.0500 (4)0.6406 (2)0.60194 (15)0.0230 (6)
C6−0.1269 (4)0.63872 (19)0.52350 (15)0.0225 (6)
H6−0.27100.64590.50730.027*
C7−0.0596 (4)0.6209 (2)0.38261 (16)0.0265 (7)
H7−0.20520.62680.36910.032*
C8−0.0031 (5)0.6428 (2)0.73701 (16)0.0328 (7)
H8A−0.03240.58110.76950.039*
H8B−0.00480.70560.77140.039*
C90.4907 (4)0.6181 (2)0.12152 (15)0.0240 (6)
C100.2786 (4)0.6096 (2)0.09607 (15)0.0247 (6)
C110.2024 (4)0.6141 (2)0.01456 (14)0.0248 (7)
H110.05910.6072−0.00340.030*
C120.3487 (4)0.6294 (2)−0.03776 (15)0.0238 (6)
C130.5577 (4)0.6389 (2)−0.01390 (15)0.0236 (6)
C140.6353 (4)0.6332 (2)0.06454 (15)0.0244 (6)
H140.77970.63890.08070.029*
C150.5696 (4)0.6118 (2)0.20578 (16)0.0283 (7)
H150.71510.61740.21960.034*
C160.5093 (4)0.6575 (2)−0.14766 (16)0.0316 (7)
H16A0.53890.6056−0.18870.038*
H16B0.50770.7277−0.17240.038*
O10.3710 (3)0.60201 (16)0.43841 (10)0.0301 (5)
H10.30940.59850.39160.045*
O20.1955 (3)0.63205 (16)0.70789 (10)0.0353 (5)
O3−0.1564 (3)0.65199 (16)0.66900 (10)0.0343 (5)
O40.0485 (3)0.60984 (15)0.32659 (10)0.0314 (5)
O50.1369 (3)0.59693 (17)0.14948 (11)0.0336 (5)
H50.19830.59200.19620.050*
O60.3117 (3)0.63578 (15)−0.11966 (11)0.0331 (5)
O70.6644 (3)0.65268 (16)−0.08064 (10)0.0330 (5)
O80.4600 (3)0.59961 (16)0.26055 (11)0.0357 (5)
U11U22U33U12U13U23
C10.0199 (15)0.0198 (14)0.0233 (15)0.0015 (12)0.0015 (12)0.0026 (11)
C20.0210 (15)0.0221 (15)0.0235 (15)−0.0035 (12)0.0041 (12)0.0004 (11)
C30.0176 (15)0.0323 (17)0.0310 (17)−0.0011 (13)0.0000 (13)0.0009 (12)
C40.0250 (16)0.0266 (15)0.0182 (15)−0.0003 (13)0.0010 (12)−0.0011 (11)
C50.0215 (15)0.0252 (15)0.0238 (16)0.0018 (13)0.0088 (12)−0.0026 (12)
C60.0158 (14)0.0247 (15)0.0262 (15)0.0011 (13)−0.0016 (12)0.0006 (12)
C70.0236 (16)0.0246 (16)0.0302 (17)0.0002 (13)−0.0020 (13)0.0032 (12)
C80.0281 (17)0.0458 (19)0.0248 (16)0.0026 (15)0.0042 (13)−0.0019 (14)
C90.0256 (15)0.0238 (15)0.0225 (15)0.0029 (14)0.0014 (12)−0.0019 (12)
C100.0223 (16)0.0248 (15)0.0276 (16)0.0002 (13)0.0055 (12)0.0007 (12)
C110.0154 (14)0.0319 (17)0.0263 (16)0.0005 (13)−0.0009 (12)0.0011 (12)
C120.0261 (16)0.0254 (15)0.0191 (14)0.0010 (13)−0.0006 (12)0.0000 (12)
C130.0223 (15)0.0252 (15)0.0238 (16)−0.0007 (13)0.0049 (12)0.0015 (12)
C140.0156 (14)0.0278 (16)0.0297 (16)−0.0017 (13)0.0020 (12)−0.0001 (12)
C150.0228 (15)0.0339 (17)0.0282 (16)0.0023 (14)0.0024 (13)−0.0019 (13)
C160.0290 (17)0.0385 (17)0.0281 (17)−0.0045 (15)0.0073 (14)0.0025 (13)
O10.0191 (11)0.0496 (13)0.0217 (11)0.0002 (10)0.0035 (8)0.0014 (10)
O20.0234 (12)0.0598 (14)0.0224 (11)0.0034 (10)0.0015 (9)−0.0048 (10)
O30.0238 (11)0.0573 (15)0.0225 (11)0.0067 (10)0.0053 (9)−0.0045 (10)
O40.0321 (12)0.0414 (12)0.0217 (11)0.0012 (10)0.0068 (9)0.0020 (9)
O50.0208 (11)0.0557 (14)0.0252 (11)−0.0006 (10)0.0061 (9)0.0015 (10)
O60.0271 (12)0.0484 (13)0.0232 (11)−0.0025 (10)−0.0003 (9)0.0039 (9)
O70.0257 (12)0.0508 (14)0.0231 (11)−0.0075 (10)0.0051 (9)0.0011 (9)
O80.0335 (13)0.0493 (14)0.0250 (11)0.0020 (11)0.0062 (9)−0.0010 (10)
C1—C21.407 (4)C9—C141.422 (3)
C1—C61.419 (3)C9—C151.447 (4)
C1—C71.438 (4)C10—O51.360 (3)
C2—O11.351 (3)C10—C111.399 (3)
C2—C31.398 (3)C11—C121.373 (4)
C3—C41.360 (3)C11—H110.9500
C3—H30.9500C12—O61.366 (3)
C4—O21.367 (3)C12—C131.378 (4)
C4—C51.389 (4)C13—C141.354 (4)
C5—C61.351 (3)C13—O71.387 (3)
C5—O31.387 (3)C14—H140.9500
C6—H60.9500C15—O81.229 (3)
C7—O41.238 (3)C15—H150.9500
C7—H70.9500C16—O71.423 (3)
C8—O31.432 (3)C16—O61.440 (3)
C8—O21.433 (3)C16—H16A0.9900
C8—H8A0.9900C16—H16B0.9900
C8—H8B0.9900O1—H10.8400
C9—C101.400 (4)O5—H50.8400
C2—C1—C6120.8 (2)O5—C10—C11116.8 (2)
C2—C1—C7121.0 (2)O5—C10—C9121.5 (2)
C6—C1—C7118.2 (3)C11—C10—C9121.6 (2)
O1—C2—C3117.4 (2)C12—C11—C10115.5 (3)
O1—C2—C1121.7 (2)C12—C11—H11122.3
C3—C2—C1120.9 (2)C10—C11—H11122.3
C4—C3—C2116.2 (3)O6—C12—C11126.0 (3)
C4—C3—H3121.9O6—C12—C13110.2 (2)
C2—C3—H3121.9C11—C12—C13123.8 (2)
C3—C4—O2126.7 (3)C14—C13—C12121.7 (2)
C3—C4—C5123.7 (2)C14—C13—O7128.3 (3)
O2—C4—C5109.6 (2)C12—C13—O7109.9 (2)
C6—C5—O3128.5 (3)C13—C14—C9116.9 (3)
C6—C5—C4121.6 (2)C13—C14—H14121.5
O3—C5—C4109.9 (2)C9—C14—H14121.5
C5—C6—C1116.8 (3)O8—C15—C9124.0 (3)
C5—C6—H6121.6O8—C15—H15118.0
C1—C6—H6121.6C9—C15—H15118.0
O4—C7—C1125.1 (3)O7—C16—O6108.3 (2)
O4—C7—H7117.5O7—C16—H16A110.0
C1—C7—H7117.5O6—C16—H16A110.0
O3—C8—O2108.1 (2)O7—C16—H16B110.0
O3—C8—H8A110.1O6—C16—H16B110.0
O2—C8—H8A110.1H16A—C16—H16B108.4
O3—C8—H8B110.1C2—O1—H1109.5
O2—C8—H8B110.1C4—O2—C8106.6 (2)
H8A—C8—H8B108.4C5—O3—C8105.6 (2)
C10—C9—C14120.4 (2)C10—O5—H5109.5
C10—C9—C15121.6 (2)C12—O6—C16105.8 (2)
C14—C9—C15118.0 (3)C13—O7—C16105.4 (2)
C6—C1—C2—O1−179.8 (2)C10—C11—C12—O6179.6 (2)
C7—C1—C2—O11.9 (4)C10—C11—C12—C130.6 (4)
C6—C1—C2—C30.8 (4)O6—C12—C13—C14−178.7 (2)
C7—C1—C2—C3−177.5 (2)C11—C12—C13—C140.4 (4)
O1—C2—C3—C4179.1 (2)O6—C12—C13—O70.4 (3)
C1—C2—C3—C4−1.4 (4)C11—C12—C13—O7179.5 (2)
C2—C3—C4—O2180.0 (2)C12—C13—C14—C9−0.8 (4)
C2—C3—C4—C51.1 (4)O7—C13—C14—C9−179.6 (2)
C3—C4—C5—C60.0 (4)C10—C9—C14—C130.1 (4)
O2—C4—C5—C6−179.0 (2)C15—C9—C14—C13−179.9 (2)
C3—C4—C5—O3179.2 (3)C10—C9—C15—O8−0.5 (4)
O2—C4—C5—O30.2 (3)C14—C9—C15—O8179.5 (3)
O3—C5—C6—C1−179.8 (2)C3—C4—O2—C8−177.1 (3)
C4—C5—C6—C1−0.7 (4)C5—C4—O2—C82.0 (3)
C2—C1—C6—C50.3 (4)O3—C8—O2—C4−3.3 (3)
C7—C1—C6—C5178.7 (2)C6—C5—O3—C8176.9 (3)
C2—C1—C7—O4−1.8 (4)C4—C5—O3—C8−2.2 (3)
C6—C1—C7—O4179.8 (3)O2—C8—O3—C53.4 (3)
C14—C9—C10—O5−178.8 (3)C11—C12—O6—C16177.0 (3)
C15—C9—C10—O51.2 (4)C13—C12—O6—C16−3.9 (3)
C14—C9—C10—C110.9 (4)O7—C16—O6—C126.0 (3)
C15—C9—C10—C11−179.1 (3)C14—C13—O7—C16−177.7 (3)
O5—C10—C11—C12178.5 (2)C12—C13—O7—C163.4 (3)
C9—C10—C11—C12−1.2 (4)O6—C16—O7—C13−5.7 (3)
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.922.652 (3)146.
O5—H5···O80.841.912.645 (3)145.
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O40.841.922.652 (3)146
O5—H5⋯O80.841.912.645 (3)145
  4 in total

1.  Synthesis and glycogen phosphorylase inhibitor activity of 2,3-dihydrobenzo[1,4]dioxin derivatives.

Authors:  László Juhász; Tibor Docsa; Attila Brunyászki; Pál Gergely; Sándor Antus
Journal:  Bioorg Med Chem       Date:  2007-04-02       Impact factor: 3.641

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Synthesis and HIV-1 integrase inhibitory activities of caffeic acid dimers derived from Salvia officinalis.

Authors:  Fabrice Bailly; Clémence Queffelec; Gladys Mbemba; Jean-François Mouscadet; Philippe Cotelle
Journal:  Bioorg Med Chem Lett       Date:  2005-09-23       Impact factor: 2.823

4.  trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist.

Authors:  Juan Pablo Cueva; Gianfabio Giorgioni; Russell A Grubbs; Benjamin R Chemel; Val J Watts; David E Nichols
Journal:  J Med Chem       Date:  2006-11-16       Impact factor: 7.446
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.