Crystal structure of (2′,3,6′-tri­chloro­biphenyl-2-yl)boronic acid tetra­hydro­furan monosolvate

Durka, K.; Kliś, T.; Serwatowski, J.

doi:10.1107/S205698901502054X

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Volume 71| Part 12| December 2015| Pages 1471-1474

https://doi.org/10.1107/S205698901502054X

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Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate

Krzysztof Durka,^a ^* Tomasz Kliś ^a and Janusz Serwatowski ^a

^aPhysical Chemistry Department, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
^*Correspondence e-mail: kdurka@ch.pw.edu.pl

Edited by J. Simpson, University of Otago, New Zealand (Received 10 October 2015; accepted 29 October 2015; online 7 November 2015)

The title compound, C₁₂H₈BCl₃O₂·C₄H₈O, crystallizes as a tetrahydrofuran monosolvate. The boronic acid group adopts a syn–anti conformation and is significantly twisted along the carbon–boron bond by 69.2 (1)°, due to considerable steric hindrance from the 2′,6′-dichlorophenyl group that is located ortho to the boronic acid substituent. The phenyl rings of the biphenyl are almost perpendicular to one another, with a dihedral angle of 87.9 (1)° between them. In the crystal, adjacent molecules are linked via O—H⋯O interactions to form centrosymmetric dimers with R₂²(8) motifs, which have recently been shown to be energetically very favourable. The hydroxy groups are in an anti conformation and are also engaged in hydrogen-bonding interactions with the O atom of the tetrahydrofuran solvent molecule. Cl⋯Cl halogen-bonding interactions [Cl⋯Cl = 3.464 (1) Å] link neigbouring dimers into chains running along [010]. Further aggregation occurs due to an additional Cl⋯Cl halogen bond [Cl⋯Cl = 3.387 (1) Å].

Keywords: arylboronic acid; hydrogen-bonding interactions; halogen-bonding interactions; biphenyl; THF solvate; crystal structure.

CCDC reference: 1434205

1. Chemical context

Boronic acids and their derivatives have been studied intensively in recent years due to their numerous applications in organic, analytical and materials chemistry (Hall, 2011 ; Furukawa & Yaghi, 2009 ). They are widely used in medicine, for example, as antifungal and antibacterical agents (Adamczyk-Woźniak et al., 2015 ; Kane et al., 2003 ; Vogt et al., 2013 ). Besides these applications, phenylboronic acids have also been studied in terms of crystal engineering (Nishiyabu et al., 2011 ; Severin, 2009 ). In contrast, biphenyl-based boronic acids have been largely neglected. Exceptions to this include reports of the crystal structures of (2-biphenylyl)boronic acid (Filthaus et al., 2008 ) and (2-methoxy-3-biphenyl)boronic acid (Davies et al., 2008 ). In this manuscript we focus our attention on a sterically hindered boronic acid derivative based on a biphenyl core with a boronic group located at the 2-position of one benzene ring with a Cl substituent at the 3-position. The second benzene ring of the biphenyl ring system carries chlorine substituents at the 2- and 6-positions. This molecule crystallized as a 1:1 solvate with THF, Fig. 1.

Figure 1
The structure of 1, showing the atom numbering, with displacement ellipsoids drawn at the 50% probability level.

2. Structural commentary

The B—C [1.5907 (16) Å] and B—O [1.3514 (14), 1.3641 (14) Å] bonds in the title compound (I) are within the expected range typically observed for boronic acids (Madura et al., 2014 ; Luliński et al., 2007 ; Maly et al., 2006 ; Shimpi et al., 2007 ; Durka et al., 2012 ). The molecular structure shows that the B(OH)₂ group adopts the usual syn–anti conformation (Fig. 1). The boronic acid substituent is significantly rotated about the C—B bond in order to minimize the steric hindrance between the boronic group and the adjacent 2′,6′-dichlorophenyl ring [τ_{C2—C1—B1—O1} = 69.2 (2)°]. In the structure of the related (2-biphenylyl)boronic acid (Filthaus et al., 2008) this torsion angle is some 20° smaller, which clearly shows the influence of the three chlorine substituents on this structure. It is also notable that in (I) the phenyl rings of the biphenyl system are almost perpendicular to one another [τ_{C1—C6—C7—C11} = 87.9 (1)°], whereas in (2-biphenylyl)boronic acid they are rotated by only 48.4 or 45.4° for the two unique molecules in the asymmetric unit.

3. Supramolecular features

In the crystal, centrosymmetric O—H⋯O hydrogen-bonded dimers are formed. The anti-oriented OH group is engaged in an intermolecular O—H⋯O hydrogen bond (Table 1) with the oxygen atom from the tetrahydrofuran solvate molecule. Because all of the hydrogen-bond acceptor centres are saturated, the syn OH group is not involved in any side hydrogen-bond interactions. Neighbouring dimers are connected through Cl⋯Cl halogen bonds [d_Cl⋯Cl = 3.464 (1) Å; the sum of the van der Waals radii for Cl is 3.50 Å]. In terms of geometry of this contact, it can be classified as a type I halogen bond (Fig. 2a), (Metrangolo et al., 2005 ; Nayak et al., 2011 ). These contacts result in the formation of molecular chains propagating along [010] (Fig. 3). A three-dimensional network forms through additional Cl⋯Cl halogen bonds (Fig. 4) of type II [d_Cl⋯Cl = 3.387 (1) Å] (Fig. 2b).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3	0.82 (1)	1.84 (1)	2.6475 (12)	169 (2)
O2—H2A⋯O1ⁱ	0.84 (1)	1.96 (1)	2.7997 (12)	175 (2)
Symmetry code: (i) -x+2, -y+1, -z+1.

Figure 2
Type I (a) and II (b) Cl⋯Cl halogen bonds in (I)

Figure 3
Molecular chains formed along b by type 1 Cl⋯Cl halogen bonds. Also shown are inversion dimers and inclusion of the solvent through O—H⋯O hydrogen bonds. Aromatic H atoms have been omitted for clarity.

Figure 4
Crystal packing showing intermolecular O—H⋯O and type II Cl⋯Cl interactions.

4. Synthesis and crystallization

Synthesis of (I) (Fig. 5): A solution of 2-iodo-2′,3,6′-trichlorobiphenyl (3.8 g, 10 mmol) in THF (50 mL) was added to a stirred solution of n-BuLi (10 mmol) in THF (30 mL) at 195 K. The resulting colorless solution was stirred for 1 h to give a colorless precipitate. The electrophile, B(OMe)₃ (2.1 g, 20 mmol) was then added to the stirred mixture to give a colorless solution which was stirred for 1 h and then hydrolyzed with H₂O (100 mL). Dilute aq. H₂SO₄ was added until the pH was slightly acidic. Et₂O (50 mL) was next added and the mixture stirred for 10 min. The organic phase was separated and the aqueous phase was extracted with Et₂O (20 mL). The combined organic solutions were dried over MgSO₄ and evaporated to give a colorless precipitate, yield 2.0 g (66%). ¹H NMR (400 MHz, acetone-d₆): δ = 8.00 (2H, s, OH), 7.51 (2H, m), 7.39 (3H, m), 7.05 (1H, m); ¹³C{1H} NMR (100.6 MHz, acetone-d₆): δ = 141.49, 139.62, 139 (br), 136.17, 134.84, 130.49, 129.99, 128.24, 128.14, 127.53.

Figure 5
The synthesis of 2-chloro-6-(2′,6′-dichlorophenyl)phenylboronic acid.

Crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a THF solution.

5. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. All CH hydrogen atoms were placed in calculated positions with C—H distances of 0.95 or 0.99 Å. They were included in the refinement in the riding-motion approximation with U_iso(phenyl H) = 1.2U_eq(C). The positions of the OH hydrogen atoms were first found in a difference map. Then their bond lengths were restrained in the last least-squares cycles, with an O—H distance of 0.85 Å and their coordinates refined with U_iso(hydroxyl H) = 1.5U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₈BCl₃O₂·C₄H₈O
M_r	373.45
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	130
a, b, c (Å)	8.3306 (3), 8.7122 (2), 12.4307 (4)
α, β, γ (°)	98.683 (3), 97.737 (3), 99.398 (3)
V (Å³)	868.07 (5)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.54
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual Source diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.795, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	28647, 6107, 5162
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.085, 1.05
No. of reflections	6107
No. of parameters	214
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.36
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS97 (Sheldrick, 2015 ), SHELXL2013 (Sheldrick, 2015), DIAMOND (Brandenburg, 2005 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1434205

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698901502054X/sj5482sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901502054X/sj5482Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901502054X/sj5482Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S205698901502054X/sj5482Isup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S205698901502054X/sj5482Isup5.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

(2',3,6'-Trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate top

Crystal data top

C₁₂H₈BCl₃O₂·C₄H₈O	F(000) = 384
M_r = 373.45	D_x = 1.429 Mg m⁻³
Triclinic, P1	Melting point: 411 K
a = 8.3306 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7122 (2) Å	Cell parameters from 14113 reflections
c = 12.4307 (4) Å	θ = 2.4–32.4°
α = 98.683 (3)°	µ = 0.54 mm⁻¹
β = 97.737 (3)°	T = 130 K
γ = 99.398 (3)°	Fragment, colourless
V = 868.07 (5) Å³	0.15 × 0.12 × 0.10 mm
Z = 2

Data collection top

Agilent SuperNova Dual Source diffractometer with an Atlas detector	6107 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5162 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 5.2195 pixels mm^-1	θ_max = 32.6°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −13→13
T_min = 0.795, T_max = 1.000	l = −18→18
28647 measured reflections

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0328P)² + 0.3549P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
6107 reflections	Δρ_max = 0.45 e Å⁻³
214 parameters	Δρ_min = −0.36 e Å⁻³

Special details top

Experimental. Absorption correction: CrysAlisPro (Agilent Technologies, 2014), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.77416 (13)	0.33187 (12)	0.22248 (8)	0.01544 (18)
C2	0.85513 (13)	0.33777 (12)	0.13113 (9)	0.01761 (19)
C3	0.77605 (15)	0.28436 (14)	0.02290 (9)	0.0221 (2)
H3	0.8355	0.2914	−0.0368	0.027*
C5	0.52304 (15)	0.21255 (15)	0.09167 (10)	0.0233 (2)
H5	0.4085	0.1690	0.0782	0.028*
C6	0.60414 (13)	0.26808 (13)	0.19972 (9)	0.01703 (19)
C7	0.50529 (13)	0.26201 (13)	0.29144 (9)	0.01742 (19)
C8	0.47656 (14)	0.12861 (13)	0.34104 (9)	0.0188 (2)
C9	0.38144 (14)	0.12012 (15)	0.42447 (10)	0.0230 (2)
H9	0.3646	0.0276	0.4565	0.028*
C10	0.31167 (15)	0.24852 (16)	0.46023 (11)	0.0263 (2)
H10	0.2466	0.2441	0.5172	0.032*
C11	0.43238 (14)	0.38827 (13)	0.33025 (10)	0.0211 (2)
C12	0.33610 (15)	0.38351 (16)	0.41341 (11)	0.0262 (2)
H12	0.2879	0.4714	0.4377	0.031*
C13	0.60897 (16)	0.22065 (15)	0.00366 (10)	0.0257 (2)
H13	0.5531	0.1825	−0.0697	0.031*
C14	0.82695 (16)	0.75012 (14)	0.14313 (10)	0.0241 (2)
H14A	0.7067	0.7154	0.1184	0.029*
H14B	0.8843	0.6702	0.1077	0.029*
C15	0.88574 (17)	0.91105 (15)	0.11452 (11)	0.0283 (3)
H15A	0.8014	0.9785	0.1202	0.034*
H15B	0.9142	0.9012	0.0393	0.034*
C16	1.03885 (18)	0.97668 (16)	0.20241 (12)	0.0325 (3)
H16A	1.1369	0.9378	0.1804	0.039*
H16B	1.0621	1.0937	0.2165	0.039*
C17	0.9899 (2)	0.91251 (17)	0.30259 (12)	0.0358 (3)
H17A	1.0868	0.8873	0.3471	0.043*
H17B	0.9443	0.9914	0.3495	0.043*
B1	0.86796 (14)	0.39672 (14)	0.34516 (10)	0.0160 (2)
O1	0.92407 (11)	0.55444 (9)	0.38238 (7)	0.02050 (16)
O2	0.89019 (11)	0.29285 (10)	0.41379 (7)	0.02293 (17)
O3	0.86646 (12)	0.77103 (10)	0.26144 (7)	0.02631 (19)
Cl1	0.56394 (4)	−0.03377 (3)	0.29838 (2)	0.02648 (7)
Cl2	0.46307 (4)	0.55927 (3)	0.27352 (3)	0.02936 (8)
Cl3	1.06696 (3)	0.41387 (4)	0.15296 (2)	0.02402 (7)
H1A	0.902 (2)	0.6121 (19)	0.3383 (13)	0.036*
H2A	0.941 (2)	0.336 (2)	0.4767 (12)	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0179 (5)	0.0142 (4)	0.0137 (4)	0.0028 (3)	0.0005 (3)	0.0028 (3)
C2	0.0196 (5)	0.0163 (4)	0.0168 (5)	0.0029 (4)	0.0027 (4)	0.0034 (4)
C3	0.0289 (6)	0.0237 (5)	0.0148 (5)	0.0061 (4)	0.0047 (4)	0.0040 (4)
C5	0.0212 (5)	0.0264 (6)	0.0181 (5)	0.0002 (4)	−0.0030 (4)	0.0013 (4)
C6	0.0186 (5)	0.0169 (4)	0.0146 (4)	0.0025 (4)	0.0002 (4)	0.0028 (4)
C7	0.0156 (4)	0.0194 (5)	0.0152 (4)	0.0009 (4)	0.0001 (3)	0.0015 (4)
C8	0.0197 (5)	0.0202 (5)	0.0150 (5)	0.0025 (4)	0.0003 (4)	0.0014 (4)
C9	0.0208 (5)	0.0284 (6)	0.0192 (5)	0.0013 (4)	0.0022 (4)	0.0065 (4)
C10	0.0186 (5)	0.0363 (7)	0.0236 (6)	0.0033 (5)	0.0060 (4)	0.0044 (5)
C11	0.0176 (5)	0.0196 (5)	0.0243 (5)	0.0016 (4)	0.0010 (4)	0.0027 (4)
C12	0.0193 (5)	0.0296 (6)	0.0293 (6)	0.0065 (4)	0.0056 (4)	0.0005 (5)
C13	0.0305 (6)	0.0290 (6)	0.0138 (5)	0.0024 (5)	−0.0024 (4)	0.0013 (4)
C14	0.0267 (6)	0.0221 (5)	0.0226 (5)	0.0031 (4)	0.0000 (4)	0.0059 (4)
C15	0.0332 (7)	0.0258 (6)	0.0278 (6)	0.0044 (5)	0.0057 (5)	0.0114 (5)
C16	0.0333 (7)	0.0243 (6)	0.0375 (7)	−0.0023 (5)	0.0049 (6)	0.0068 (5)
C17	0.0411 (8)	0.0261 (6)	0.0328 (7)	−0.0066 (5)	−0.0064 (6)	0.0072 (5)
B1	0.0152 (5)	0.0170 (5)	0.0146 (5)	0.0022 (4)	0.0009 (4)	0.0015 (4)
O1	0.0278 (4)	0.0162 (4)	0.0149 (4)	0.0019 (3)	−0.0030 (3)	0.0027 (3)
O2	0.0302 (4)	0.0179 (4)	0.0170 (4)	0.0010 (3)	−0.0053 (3)	0.0036 (3)
O3	0.0328 (5)	0.0202 (4)	0.0233 (4)	−0.0005 (3)	−0.0017 (3)	0.0072 (3)
Cl1	0.04097 (17)	0.02093 (13)	0.02001 (13)	0.00986 (11)	0.00736 (11)	0.00481 (10)
Cl2	0.02627 (15)	0.02037 (13)	0.04284 (18)	0.00462 (10)	0.00663 (12)	0.00884 (12)
Cl3	0.01988 (13)	0.02816 (14)	0.02462 (14)	0.00239 (10)	0.00640 (10)	0.00636 (11)

Geometric parameters (Å, º) top

C1—C2	1.3999 (15)	C11—Cl2	1.7388 (12)
C1—C6	1.4081 (15)	C12—H12	0.9500
C1—B1	1.5907 (16)	C13—H13	0.9500
C2—C3	1.3902 (16)	C14—O3	1.4400 (15)
C2—Cl3	1.7498 (11)	C14—C15	1.5183 (17)
C3—C13	1.3859 (18)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C5—C13	1.3900 (17)	C15—C16	1.532 (2)
C5—C6	1.3954 (15)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.4959 (15)	C16—C17	1.517 (2)
C7—C11	1.3959 (16)	C16—H16A	0.9900
C7—C8	1.3976 (15)	C16—H16B	0.9900
C8—C9	1.3908 (16)	C17—O3	1.4465 (16)
C8—Cl1	1.7395 (12)	C17—H17A	0.9900
C9—C10	1.3851 (18)	C17—H17B	0.9900
C9—H9	0.9500	B1—O2	1.3514 (14)
C10—C12	1.3869 (19)	B1—O1	1.3641 (14)
C10—H10	0.9500	O1—H1A	0.821 (14)
C11—C12	1.3924 (17)	O2—H2A	0.838 (14)

C2—C1—C6	116.31 (9)	C3—C13—C5	120.03 (11)
C2—C1—B1	121.95 (9)	C3—C13—H13	120.0
C6—C1—B1	121.73 (9)	C5—C13—H13	120.0
C3—C2—C1	123.29 (10)	O3—C14—C15	105.36 (10)
C3—C2—Cl3	117.77 (9)	O3—C14—H14A	110.7
C1—C2—Cl3	118.93 (8)	C15—C14—H14A	110.7
C13—C3—C2	118.82 (11)	O3—C14—H14B	110.7
C13—C3—H3	120.6	C15—C14—H14B	110.7
C2—C3—H3	120.6	H14A—C14—H14B	108.8
C13—C5—C6	120.36 (11)	C14—C15—C16	102.13 (10)
C13—C5—H5	119.8	C14—C15—H15A	111.3
C6—C5—H5	119.8	C16—C15—H15A	111.3
C5—C6—C1	121.18 (10)	C14—C15—H15B	111.3
C5—C6—C7	118.41 (10)	C16—C15—H15B	111.3
C1—C6—C7	120.40 (9)	H15A—C15—H15B	109.2
C11—C7—C8	116.15 (10)	C17—C16—C15	102.58 (11)
C11—C7—C6	121.66 (10)	C17—C16—H16A	111.3
C8—C7—C6	122.17 (10)	C15—C16—H16A	111.3
C9—C8—C7	122.68 (11)	C17—C16—H16B	111.3
C9—C8—Cl1	118.09 (9)	C15—C16—H16B	111.3
C7—C8—Cl1	119.23 (9)	H16A—C16—H16B	109.2
C10—C9—C8	119.03 (11)	O3—C17—C16	106.63 (11)
C10—C9—H9	120.5	O3—C17—H17A	110.4
C8—C9—H9	120.5	C16—C17—H17A	110.4
C9—C10—C12	120.49 (11)	O3—C17—H17B	110.4
C9—C10—H10	119.8	C16—C17—H17B	110.4
C12—C10—H10	119.8	H17A—C17—H17B	108.6
C12—C11—C7	122.63 (11)	O2—B1—O1	119.71 (10)
C12—C11—Cl2	118.30 (9)	O2—B1—C1	118.96 (9)
C7—C11—Cl2	119.07 (9)	O1—B1—C1	121.33 (9)
C10—C12—C11	119.01 (12)	B1—O1—H1A	115.3 (13)
C10—C12—H12	120.5	B1—O2—H2A	113.1 (12)
C11—C12—H12	120.5	C14—O3—C17	109.77 (10)

C6—C1—C2—C3	−0.15 (16)	Cl1—C8—C9—C10	179.55 (9)
B1—C1—C2—C3	−178.97 (10)	C8—C9—C10—C12	0.09 (18)
C6—C1—C2—Cl3	−179.42 (8)	C8—C7—C11—C12	−0.07 (17)
B1—C1—C2—Cl3	1.76 (14)	C6—C7—C11—C12	178.17 (11)
C1—C2—C3—C13	−0.56 (17)	C8—C7—C11—Cl2	179.60 (8)
Cl3—C2—C3—C13	178.72 (9)	C6—C7—C11—Cl2	−2.15 (15)
C13—C5—C6—C1	−0.63 (18)	C9—C10—C12—C11	−0.26 (19)
C13—C5—C6—C7	177.91 (11)	C7—C11—C12—C10	0.25 (18)
C2—C1—C6—C5	0.74 (16)	Cl2—C11—C12—C10	−179.42 (10)
B1—C1—C6—C5	179.56 (10)	C2—C3—C13—C5	0.69 (18)
C2—C1—C6—C7	−177.77 (9)	C6—C5—C13—C3	−0.11 (19)
B1—C1—C6—C7	1.05 (15)	O3—C14—C15—C16	33.84 (13)
C5—C6—C7—C11	−90.69 (13)	C14—C15—C16—C17	−35.53 (14)
C1—C6—C7—C11	87.86 (13)	C15—C16—C17—O3	25.23 (15)
C5—C6—C7—C8	87.44 (14)	C2—C1—B1—O2	−111.66 (12)
C1—C6—C7—C8	−94.00 (13)	C6—C1—B1—O2	69.59 (14)
C11—C7—C8—C9	−0.11 (16)	C2—C1—B1—O1	69.17 (14)
C6—C7—C8—C9	−178.35 (10)	C6—C1—B1—O1	−109.58 (12)
C11—C7—C8—Cl1	−179.56 (8)	C15—C14—O3—C17	−18.86 (14)
C6—C7—C8—Cl1	2.21 (14)	C16—C17—O3—C14	−4.30 (16)
C7—C8—C9—C10	0.10 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3	0.82 (1)	1.84 (1)	2.6475 (12)	169 (2)
O2—H2A···O1ⁱ	0.84 (1)	1.96 (1)	2.7997 (12)	175 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

The X-ray measurements were undertaken in the Crystallographic Unit of the Physical Chemistry Laboratory at the Chemistry Department of the University of Warsaw. This work was supported by the Aldrich Chemical Company through the donation of chemicals and equipment, and by the Warsaw University of Technology.

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