Literature DB >> 21201442

(2-Meth-oxy-1,3-phenyl-ene)diboronic acid.

Marek Dąbrowski¹, Sergiusz Luliński, Janusz Serwatowski.

Abstract

The mol-ecular structure of the title compound, 2-CH(3)O-C(6)H(3)-1,3-[B(OH)(2)](2) or C(7)H(10)B(2)O(5), features two intra-molecular O-H⋯O hydrogen bonds of different strengths. One of the boronic acid groups is almost coplanar with the aromatic ring, whereas the second is significantly twisted. Mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds, generating infinite chains cross-linked to form a two-dimensional sheet structure aligned parallel to the (01) plane.

Entities: CellLine Chemical Disease Gene

Year: 2008 PMID： 21201442 PMCID： PMC2960205 DOI： 10.1107/S160053680800010X

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

Related literature

For structures of other di- and polyboronic acids, see: Fournier et al. (2003 ▶); Maly et al. (2006 ▶); Pilkington et al. (1995 ▶); Rodríguez-Cuamatzi, Vargas-Díaz, Maris, Wuest & Höpfl (2004 ▶); Rodríguez-Cuamatzi, Vargas-Díaz & Höpfl (2004 ▶). For the structural characterization of related ortho-alkoxy arylboronic acids, see: Dabrowski et al. (2006 ▶); Serwatowski et al. (2006 ▶); Yang et al. (2005 ▶). For related literature, see: Rettig & Trotter (1977 ▶); Dorman (1966 ▶).

Experimental

Crystal data

C7H10B2O5 M = 195.77 Triclinic, a = 5.0261 (6) Å b = 7.6475 (12) Å c = 12.4535 (19) Å α = 79.010 (13)° β = 81.898 (12)° γ = 77.246 (12)° V = 455.85 (11) Å3 Z = 2 Mo Kα radiation μ = 0.12 mm−1 T = 100 (2) K 0.75 × 0.28 × 0.16 mm

Data collection

Kuma KM4 CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005 ▶) T min = 0.91, T max = 0.98 8626 measured reflections 2191 independent reflections 1884 reflections with I > 2σ(I) R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.099 S = 1.17 2191 reflections 168 parameters All H-atom parameters refined Δρmax = 0.40 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction (2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction (2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800010X/om2204sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680800010X/om2204Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₇H₁₀B₂O₅	Z = 2
M_r = 195.77	F₀₀₀ = 204
Triclinic, P1	D_x = 1.426 Mg m⁻³
a = 5.0261 (6) Å	Melting point: 670 K
b = 7.6475 (12) Å	Mo Kα radiation λ = 0.71073 Å
c = 12.4535 (19) Å	µ = 0.12 mm⁻¹
α = 79.010 (13)º	T = 100 (2) K
β = 81.898 (12)º	Prismatic, colourless
γ = 77.246 (12)º	0.75 × 0.28 × 0.16 mm
V = 455.85 (11) Å³

Kuma KM4 CCD diffractometer	2191 independent reflections
Radiation source: fine-focus sealed tube	1884 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.012
Detector resolution: 8.6479 pixels mm^-1	θ_max = 28.6º
T = 100(2) K	θ_min = 2.8º
ω scans	h = −6→6
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction 2005)	k = −10→10
T_min = 0.91, T_max = 0.98	l = −16→16
8626 measured reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0674P)² + 0.0064P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max = 0.001
S = 1.17	Δρ_max = 0.40 e Å⁻³
2191 reflections	Δρ_min = −0.24 e Å⁻³
168 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.074 (12)
Secondary atom site location: difference Fourier map

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.

	x	y	z	U_iso*/U_eq
B1	0.2297 (2)	1.01153 (14)	0.88850 (8)	0.0121 (2)
O2	0.17562 (14)	1.15369 (9)	0.94414 (6)	0.01497 (19)
O3	0.44802 (13)	0.87075 (9)	0.91170 (6)	0.01494 (18)
O4	0.27015 (13)	0.71276 (8)	0.76769 (5)	0.01290 (18)
C5	0.1659 (2)	0.56730 (13)	0.84048 (9)	0.0204 (2)
B6	−0.0649 (2)	0.70611 (14)	0.59403 (8)	0.0119 (2)
O7	0.18385 (13)	0.59475 (9)	0.57331 (6)	0.01505 (19)
O8	−0.28690 (13)	0.67665 (10)	0.55374 (6)	0.01734 (19)
C9	0.04151 (18)	1.01375 (12)	0.79683 (7)	0.0114 (2)
C10	0.06518 (18)	0.86766 (12)	0.74123 (7)	0.0108 (2)
C11	−0.10218 (18)	0.86757 (12)	0.66004 (7)	0.0117 (2)
C12	−0.30411 (19)	1.02389 (13)	0.63595 (8)	0.0142 (2)
C13	−0.33351 (19)	1.17323 (13)	0.68851 (8)	0.0154 (2)
C14	−0.16146 (19)	1.16694 (12)	0.76789 (8)	0.0138 (2)
H2	0.285 (3)	1.140 (2)	0.9942 (13)	0.042 (4)*
H3	0.468 (3)	0.793 (2)	0.8674 (14)	0.048 (4)*
H5A	0.086 (3)	0.6033 (17)	0.9132 (11)	0.029 (3)*
H5B	0.322 (3)	0.4681 (19)	0.8490 (11)	0.034 (4)*
H5C	0.019 (3)	0.5290 (19)	0.8100 (12)	0.038 (4)*
H7	0.322 (3)	0.6297 (19)	0.5953 (12)	0.039 (4)*
H8	−0.239 (4)	0.591 (3)	0.5115 (15)	0.058 (5)*
H12	−0.422 (3)	1.0288 (16)	0.5792 (10)	0.023 (3)*
H13	−0.479 (3)	1.2810 (18)	0.6688 (10)	0.023 (3)*
H14	−0.189 (2)	1.2703 (16)	0.8053 (10)	0.019 (3)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0127 (5)	0.0138 (5)	0.0112 (5)	−0.0050 (4)	−0.0012 (4)	−0.0024 (4)
O2	0.0170 (4)	0.0154 (4)	0.0149 (4)	−0.0025 (3)	−0.0059 (3)	−0.0060 (3)
O3	0.0150 (4)	0.0160 (4)	0.0163 (4)	−0.0011 (3)	−0.0059 (3)	−0.0080 (3)
O4	0.0131 (3)	0.0111 (3)	0.0149 (3)	−0.0003 (3)	−0.0039 (2)	−0.0039 (3)
C5	0.0258 (5)	0.0139 (5)	0.0208 (5)	−0.0040 (4)	−0.0052 (4)	0.0011 (4)
B6	0.0123 (5)	0.0141 (5)	0.0101 (5)	−0.0033 (4)	−0.0019 (4)	−0.0032 (4)
O7	0.0110 (3)	0.0184 (4)	0.0190 (4)	−0.0020 (3)	−0.0037 (3)	−0.0105 (3)
O8	0.0116 (3)	0.0228 (4)	0.0217 (4)	−0.0018 (3)	−0.0031 (3)	−0.0144 (3)
C9	0.0118 (4)	0.0133 (4)	0.0107 (4)	−0.0045 (3)	−0.0010 (3)	−0.0034 (3)
C10	0.0094 (4)	0.0116 (4)	0.0114 (4)	−0.0021 (3)	−0.0011 (3)	−0.0020 (3)
C11	0.0116 (4)	0.0142 (4)	0.0111 (4)	−0.0038 (3)	−0.0011 (3)	−0.0047 (3)
C12	0.0141 (4)	0.0173 (5)	0.0124 (4)	−0.0030 (4)	−0.0042 (3)	−0.0036 (4)
C13	0.0154 (5)	0.0139 (5)	0.0160 (5)	0.0009 (4)	−0.0046 (3)	−0.0027 (4)
C14	0.0159 (5)	0.0124 (5)	0.0147 (5)	−0.0032 (4)	−0.0023 (3)	−0.0051 (4)

B1—O2	1.3564 (12)	B6—C11	1.5738 (13)
B1—O3	1.3768 (12)	O7—H7	0.888 (15)
B1—C9	1.5774 (13)	O8—H8	0.89 (2)
O2—H2	0.865 (17)	C9—C10	1.3982 (13)
O3—H3	0.866 (16)	C9—C14	1.3993 (13)
O4—C10	1.4075 (11)	C10—C11	1.4036 (12)
O4—C5	1.4397 (12)	C11—C12	1.4009 (13)
C5—H5A	1.001 (13)	C12—C13	1.3920 (13)
C5—H5B	0.965 (14)	C12—H12	0.975 (12)
C5—H5C	0.995 (15)	C13—C14	1.3899 (13)
B6—O8	1.3635 (12)	C13—H13	0.991 (13)
B6—O7	1.3704 (12)	C14—H14	0.967 (12)

O2—B1—O3	119.76 (8)	C10—C9—B1	123.17 (8)
O2—B1—C9	118.66 (8)	C14—C9—B1	120.01 (8)
O3—B1—C9	121.57 (8)	C9—C10—C11	123.70 (8)
B1—O2—H2	112.8 (10)	C9—C10—O4	117.99 (8)
B1—O3—H3	110.6 (11)	C11—C10—O4	118.30 (8)
C10—O4—C5	113.05 (7)	C12—C11—C10	116.72 (8)
O4—C5—H5A	111.6 (8)	C12—C11—B6	119.95 (8)
O4—C5—H5B	105.1 (8)	C10—C11—B6	123.29 (8)
H5A—C5—H5B	110.9 (11)	C13—C12—C11	121.55 (8)
O4—C5—H5C	112.4 (9)	C13—C12—H12	119.7 (7)
H5A—C5—H5C	106.8 (11)	C11—C12—H12	118.7 (7)
H5B—C5—H5C	110.0 (12)	C14—C13—C12	119.49 (8)
O8—B6—O7	118.14 (8)	C14—C13—H13	121.7 (7)
O8—B6—C11	119.17 (8)	C12—C13—H13	118.8 (7)
O7—B6—C11	122.67 (8)	C13—C14—C9	121.71 (8)
B6—O7—H7	113.0 (9)	C13—C14—H14	118.3 (7)
B6—O8—H8	111.4 (12)	C9—C14—H14	119.9 (7)
C10—C9—C14	116.81 (8)

O2—B1—C9—C10	−174.50 (8)	C9—C10—C11—B6	177.05 (8)
O3—B1—C9—C10	6.46 (14)	O4—C10—C11—B6	−2.39 (13)
O2—B1—C9—C14	5.35 (14)	O8—B6—C11—C12	−29.98 (13)
O3—B1—C9—C14	−173.69 (8)	O7—B6—C11—C12	148.79 (9)
C14—C9—C10—C11	−0.27 (14)	O8—B6—C11—C10	152.40 (9)
B1—C9—C10—C11	179.58 (8)	O7—B6—C11—C10	−28.83 (14)
C14—C9—C10—O4	179.17 (7)	C10—C11—C12—C13	1.22 (14)
B1—C9—C10—O4	−0.99 (13)	B6—C11—C12—C13	−176.55 (8)
C5—O4—C10—C9	100.68 (9)	C11—C12—C13—C14	−0.88 (15)
C5—O4—C10—C11	−79.86 (10)	C12—C13—C14—C9	−0.10 (15)
C9—C10—C11—C12	−0.64 (14)	C10—C9—C14—C13	0.65 (14)
O4—C10—C11—C12	179.93 (7)	B1—C9—C14—C13	−179.20 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.865 (17)	1.881 (17)	2.7403 (10)	172.1 (15)
O3—H3···O4	0.866 (16)	1.953 (16)	2.6890 (10)	142.1 (14)
O7—H7···O8ⁱⁱ	0.888 (15)	2.055 (15)	2.8324 (10)	145.6 (13)
O7—H7···O4	0.888 (15)	2.317 (14)	2.8573 (10)	119.1 (12)
O8—H8···O7ⁱⁱⁱ	0.89 (2)	1.88 (2)	2.7615 (10)	172.6 (18)

Table 1

Selected torsion angles (°)

O3—B1—C9—C10	6.46 (14)
C5—O4—C10—C9	100.68 (9)
O7—B6—C11—C12	148.79 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.865 (17)	1.881 (17)	2.7403 (10)	172.1 (15)
O3—H3⋯O4	0.866 (16)	1.953 (16)	2.6890 (10)	142.1 (14)
O7—H7⋯O8ⁱⁱ	0.888 (15)	2.055 (15)	2.8324 (10)	145.6 (13)
O7—H7⋯O4	0.888 (15)	2.317 (14)	2.8573 (10)	119.1 (12)
O8—H8⋯O7ⁱⁱⁱ	0.89 (2)	1.88 (2)	2.7615 (10)	172.6 (18)

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

5 in total

1. Modification of 2D water that contains hexameric units in chair and boat conformations--a contribution to the structural elucidation of bulk water.

Authors: Patricia Rodríguez-Cuamatzi; Gabriela Vargas-Díaz; Herbert Höpfl
Journal: Angew Chem Int Ed Engl Date: 2004-06-07 Impact factor: 15.336

2. A convenient preparation of xanthene dyes.

Authors: Youjun Yang; Jorge O Escobedo; Alexander Wong; Corin M Schowalter; Michael C Touchy; Lijuan Jiao; William E Crowe; Frank R Fronczek; Robert M Strongin
Journal: J Org Chem Date: 2005-08-19 Impact factor: 4.354

3. A short history of SHELX.

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

4. (2-Methoxy-3-pyridyl)boronic acid.

Authors: Marek Dabrowski; Sergiusz Lulinski; Janusz Serwatowski; Magdalena Szczerbinska
Journal: Acta Crystallogr C Date: 2006-11-30 Impact factor: 1.172

5. Molecular tectonics. Use of the hydrogen bonding of boronic acids to direct supramolecular construction.

Authors: Jean-Hugues Fournier; Thierry Maris; James D Wuest; Wenzhuo Guo; Elena Galoppini
Journal: J Am Chem Soc Date: 2003-01-29 Impact factor: 15.419