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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2681
https://doi.org/10.1107/S1600536811037019

6-Hy­dr­oxy-2H-1,3-benzodioxole-5-carbaldehyde

Mehbub I. K. Momin,a Neil Koorbanally,a Deresh Ramjugernathb and Muhammad D. Balaa*

aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa, and bSchool of Chemical Engineering, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa
*Correspondence e-mail: bala@ukzn.ac.za

(Received 8 September 2011; accepted 12 September 2011; online 17 September 2011)

The title compound, C8H6O4, crystallizes with two independent mol­ecules in the asymmetric unit. The benzodioxole ring system is almost planar in each mol­ecule, with maximum deviations of 0.008 (1) and 0.007 (1) Å. The mol­ecular structure is characterized by strong electrostatic intra­molecular O⋯O contacts [2.649 (3) Å] and intra­molecular O—H⋯O hydrogen-bonding inter­actions. Inter­molecular O⋯O inter­actions [3.001 (2) Å] are observed in the crystal structure.

Related literature

For the preparation, see: Juhász et al. (2007[Juhász, L., Docsa, T., Brunyászki, A., Gergely, P. & Antus, S. (2007). Bioorg. Med. Chem. 15, 4048-4056.]); Akselsen et al. (2009[Akselsen, Ø. W., Skattebøl, L. & Hansen, T. V. (2009). Tetrahedron Lett. 50, 6339-6341.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). 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[Bailly, F., Queffelec, C., Mbemba, G., Mouscadet, J.-F. & Cotelle, P. (2005). Bioorg. Med. Chem. Lett. 15, 5053-5056.]), dopamine D1 receptor full agonist (Cueva, et al. 2006[Cueva, J. P., Giorgioni, G., Grubbs, R. A., Chemel, B. R., Watts, V. J. & Nichols, D. E. (2006). J. Med. Chem. 49, 6848-6857.]) and glycogen phospho­rylase inhibitory activity (Juhász et al., 2007[Juhász, L., Docsa, T., Brunyászki, A., Gergely, P. & Antus, S. (2007). Bioorg. Med. Chem. 15, 4048-4056.]).

[Scheme 1]

Experimental

Crystal data

  • C8H6O4

  • Mr = 166.13

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.081
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O4 0.84 1.92 2.652 (3) 146
O5—H5⋯O8 0.84 1.91 2.645 (3) 145

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037019/qm2028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037019/qm2028Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037019/qm2028Isup3.cml

checkCIF report


Comment top

The title compound 6- hydroxybenzo[d][1,3]dioxole-5-carbaldehyde was obtained as an intermediate product in our research effort aimed at the total synthesis of biologically active compounds. These compounds have been used for HIV-1 integrase inhibitory activities as reported by Bailly et al. (2005), Dopamine D1 receptor full agonist (Cueva, et al. 2006) and glycogen phosphorylase inhibitory activity reported by Juhász et al. (2007). The compound has been previously reported by Juhász et al. (2007) and Akselsen et al. (2009) with 45% yield when it was respectively utilized as a starting material and as an intermediate in the synthesis of the biologically active compounds. However, inspite of the varied biological applications of (I) the crystal structure of the title compound has not been reported to date. The compound has two independent molecules in the asymmetric unit that are related by a crystallographic centre of inversion and a glide plane perpendicular to the (0, 1, 0) axis. The benzodioxole ring systems in the title compound are almost planar and show strong pi-pi interactions in the unit cell. The molecule is stabilized by intra-molecular hydrogen bonding contacts which are however balanced by a network of O···O electrostatic contacts that are both intra- [O1···O4 & O5···O8 = 2.649 (3) Å] and inter-molecular [O4···O8 = 3.001 (2) Å] in nature.

Related literature top

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 top

The compound 2-yydroxy-4,5-methylenedioxybenzaldehyde was synthesized by following the literature method of Akselsen et al. (2009). Brown crystals suitable for X-ray diffraction were grown from hexane:ethyl acetate (95:5). m.p. 125–127 °C. 1H NMR: δ (p.p.m.): 6.01 (2H,s, O–CH2–O); 6.46 (1H, s, H-5); 6.86 (1H, s, H-8); 9.62 (1H, s, CHO); 11.79 (1H, s, OH). 13C NMR: δ = 98.37, 102.15, 109.35, 113.65, 141.33, 155.17, 161.54, 193.69. HRMS m/z 166.0264 (calcd for C8H6O4: 166.0266).

Refinement top

All H-atoms were refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic, C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for CH2.

Structure description top

The title compound 6- hydroxybenzo[d][1,3]dioxole-5-carbaldehyde was obtained as an intermediate product in our research effort aimed at the total synthesis of biologically active compounds. These compounds have been used for HIV-1 integrase inhibitory activities as reported by Bailly et al. (2005), Dopamine D1 receptor full agonist (Cueva, et al. 2006) and glycogen phosphorylase inhibitory activity reported by Juhász et al. (2007). The compound has been previously reported by Juhász et al. (2007) and Akselsen et al. (2009) with 45% yield when it was respectively utilized as a starting material and as an intermediate in the synthesis of the biologically active compounds. However, inspite of the varied biological applications of (I) the crystal structure of the title compound has not been reported to date. The compound has two independent molecules in the asymmetric unit that are related by a crystallographic centre of inversion and a glide plane perpendicular to the (0, 1, 0) axis. The benzodioxole ring systems in the title compound are almost planar and show strong pi-pi interactions in the unit cell. The molecule is stabilized by intra-molecular hydrogen bonding contacts which are however balanced by a network of O···O electrostatic contacts that are both intra- [O1···O4 & O5···O8 = 2.649 (3) Å] and inter-molecular [O4···O8 = 3.001 (2) Å] in nature.

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
6-Hydroxy-2H-1,3-benzodioxole-5-carbaldehyde top
Crystal data top
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
Data collection top
Bruker APEXII CCD
diffractometer		1348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.081
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
φ and ω scansh = −7→8
10746 measured reflectionsk = −15→15
2708 independent reflectionsl = −18→20
Refinement top
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 = 0.94 w = 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
Crystal data top
C8H6O4V = 1382.99 (12) Å3
Mr = 166.13Z = 8
Monoclinic, P21/cMo Kα radiation
a = 6.4916 (3) ŵ = 0.13 mm−1
b = 12.8242 (7) ÅT = 173 K
c = 16.7122 (8) Å0.38 × 0.11 × 0.10 mm
β = 96.258 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		1348 reflections with I > 2σ(I)
10746 measured reflectionsRint = 0.081
2708 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 0.94Δρmax = 0.19 e Å−3
2708 reflectionsΔρmin = −0.31 e Å−3
219 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
Atomic displacement parameters (Å2) top
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)
Geometric parameters (Å, º) top
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)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.922.652 (3)146
O5—H5···O80.841.912.645 (3)145

Experimental details

Crystal data
Chemical formulaC8H6O4
Mr166.13
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)6.4916 (3), 12.8242 (7), 16.7122 (8)
β (°) 96.258 (3)
V (Å3)1382.99 (12)
Z8
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.38 × 0.11 × 0.10
Data collection
DiffractometerBruker APEXII CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		10746, 2708, 1348
Rint0.081
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.125, 0.94
No. of reflections2708
No. of parameters219
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.922.652 (3)145.7
O5—H5···O80.841.912.645 (3)145.3
 

Acknowledgements

We wish to thank Dr Manuel Fernandes (University of the Witwatersrand) for the data collection and the NRF and the University of KwaZulu-Natal for financial support. This work is based upon research supported by the South African Research Chairs Initiative of the Department of Science and Technology.

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2681
https://doi.org/10.1107/S1600536811037019
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