(2,4,6-Trimethyl­phen­yl)boronic acid–triphenyl­phosphine oxide (1/1)

Roşca, S.; Olaru, M.; Raţ, C.I.

doi:10.1107/S1600536811051609

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o31

doi:10.1107/S1600536811051609

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(2,4,6-Trimethylphenyl)boronic acid–triphenylphosphine oxide (1/1)

Sorin Roşca,^a Marian Olaru ^a and Ciprian I. Raţ ^a ^*

^aUniversitatea Babeş-Bolyai, Facultatea de Chimie şi Inginerie Chimicã, 11 Arany Janos, 400028 Cluj-Napoca, Romania
^*Correspondence e-mail: ciprian.rat@ubbcluj.ro

(Received 20 November 2011; accepted 30 November 2011; online 7 December 2011)

In the crystal structure of the title compound, C₉H₁₃BO₂·C₁₈H₁₅OP, there are O—H⋯O hydrogen bonds between the O atom of triphenylphosphine oxide and one hydroxy group of the boronic acid. Boronic acid molecules form inversion-related hydrogen-bonded dimers in an R₂²(8) motif. The structure is consolidated by intermolecular C—H⋯O bonds and C—H⋯π interactions.

Related literature

For applications of boronic acids, see: Suzuki (2011 ); Yang et al. (2011 ); Furukawa & Yaghi (2009 ). For recently reported structures of triphenylphosphine oxide and triphenylphosphine oxide hemihydrate, see: Sivaramkrishna et al. (2007 ); Ng (2009 ). For structures of related boronic acids, see: Filthaus et al. (2008 ), Cyrański et al. (2008 ); Rettig & Trotter (1977 ).

Experimental

Crystal data

C₉H₁₃BO₂·C₁₈H₁₅OP
M_r = 442.27
Monoclinic, P 2₁ /c
a = 12.218 (4) Å
b = 12.339 (4) Å
c = 16.983 (5) Å
β = 95.651 (5)°
V = 2548.0 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 297 K
0.52 × 0.45 × 0.42 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.934, T_max = 0.947
23787 measured reflections
4486 independent reflections
3727 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.186
S = 1.19
4486 reflections
294 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C19–C24 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	1.84	2.645 (3)	168
O3—H3A⋯O2ⁱ	0.82	1.99	2.795 (4)	169
C4—H4⋯O1ⁱⁱ	0.93	2.41	3.326 (4)	167
C6—H6⋯Cg4	0.93	2.88	3.728 (4)	152
C15—H15⋯Cg4ⁱⁱⁱ	0.93	2.69	3.602 (5)	168
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811051609/pk2368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051609/pk2368Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051609/pk2368Isup3.cml

checkCIF report

Comment top

Boronic acids are widely used as starting materials in Suzuki-Miyaura cross-coupling reactions (Suzuki, 2011), as sensors or binders for carbohydrates (Yang et al., 2011) or building blocks for covalent organic frameworks (Furukawa & Yaghi, 2009). Although there are a large number of reported crystal structures for aromatic boronic acids, the structure of mesitylboronic acid has not been reported yet. We present here the crystal structure of the mesityl boronic acid - triphenylphosphine oxide (1:1) adduct.

In the title compound there is an O—H···O bond between the hydrogen atom of a hydroxy group and the oxygen atom of the triphenylphosphine oxide (Fig. 1). The triphenylphosphine oxide molecules are connected into chains by weak C—H···O hydrogen bonds along the c axis direction (Table 1 and Fig. 2). The P═O bond length (1.479 (2) Å) is in the range of the values found for triphenylphosphine oxide (1.4863 (12) Å) (Sivaramkrishna et al., 2007), or triphenylphosphine oxide hemidydrate (1.4871 (15) Å) (Ng, 2009).

The molecules of the mesitylboronic acid assemble into centrosymmetric dimers through a pair of O—H···O bonds between the hydroxy groups (Fig. 2). In contrast to the structure of phenylboronic acid where the centrosymmetric dimers are interconnected to one-dimensional chains (Rettig & Trotter, 1977; Cyrański et al. 2008), in the structure of the title compound, the triphenylphosphine oxide molecules block further assembly of the dimers.

In comparison to phenylboronic acid, where the angles between the BO₂ plane and the aromatic ring plane are 6.6° and 21.4° (Rettig & Trotter, 1977) or 6.3° and 21.0° (Cyrański et al., 2008), in the title compound the angle is 75.0 (2)°. This value is close to the values found for the related pentamethylphenylboronic acid (74.7°, 85.9°) (Filthaus et al., 2008).

The mesitylboronic dimers and the triphenylphosphine oxide chains are interconnected, additionally to the O—H···O bonds, through C—H···π interactions (Table 1 and Fig. 2). In the crystal there are alternate layers of mesitylboronic acid and triphenylphosphine oxide along the a-axis (Fig. 3).

Related literature top

For applications of boronic acids, see: Suzuki (2011); Yang et al. (2011); Furukawa & Yaghi (2009). For recently reported structures of triphenylphosphine oxide and triphenylphosphine oxide hemihydrate, see: Sivaramkrishna et al. (2007); Ng (2009). For structures of related boronic acids, see: Filthaus et al. (2008), Cyrański et al. (2008); Rettig & Trotter (1977).

Experimental top

The title compound was serendipitously obtained in a Suzuki-Miyaura cross-coupling reaction between mesitylboronic acid and tert-butyl N-(tert-butoxycarbonyl)-N-(2,4,6- tribromophenyl)carbamate using tetrakis(triphenlyphosphine)palladium as catalyst. Prior to column chromatography of the crude product mixture a solid precipitated from the mobile phase (diethyl ether: petroleum ether = 1:8). Colourless crystals were obtained by recrystallization of the precipitate from hot toluene.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Crystal structure of the title compound with ellipsoids of non-hydrogen atoms drawn at the 25% probability level.
	Fig. 2. Intramolecular and intermolecular hydrogen bonds and C—H···π interactions in the structure of the title compound shown as dashed lines. Symmetry codes: (i) -x+1, -y, -z; (ii) x, -y+1/2, z+1/2; (iii) x+1, y, z; (iv) x-1, y, z; (v) x, -y+1/2, z-1/2; (vi) -x+1, y-1/2, -z-1/2; (vii) -x, -y, -z; (viii) -x+2, -y, -z; (ix) -x+1, y-1/2, -z+1/2
	Fig. 3. Capped stick representation of the crystal packing of the title compound, viewed along the c axis. Hydrogen bonds and C—H···π interactions shown as dashed lines (blue and green, respectively).

(2,4,6-Trimethylphenyl)boronic acid–triphenylphosphine oxide (1/1) top

Crystal data top

C₉H₁₃BO₂·C₁₈H₁₅OP	F(000) = 936
M_r = 442.27	D_x = 1.153 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 401 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.218 (4) Å	Cell parameters from 7170 reflections
b = 12.339 (4) Å	θ = 2.2–26.0°
c = 16.983 (5) Å	µ = 0.13 mm⁻¹
β = 95.651 (5)°	T = 297 K
V = 2548.0 (14) Å³	Block, colourless
Z = 4	0.52 × 0.45 × 0.42 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	3727 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
T_min = 0.934, T_max = 0.947	k = −14→14
23787 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0654P)² + 1.8657P] where P = (F_o² + 2F_c²)/3
4486 reflections	(Δ/σ)_max < 0.001
294 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₉H₁₃BO₂·C₁₈H₁₅OP	V = 2548.0 (14) Å³
M_r = 442.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.218 (4) Å	µ = 0.13 mm⁻¹
b = 12.339 (4) Å	T = 297 K
c = 16.983 (5) Å	0.52 × 0.45 × 0.42 mm
β = 95.651 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4486 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3727 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.947	R_int = 0.052
23787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.19	Δρ_max = 0.40 e Å⁻³
4486 reflections	Δρ_min = −0.32 e Å⁻³
294 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

	x	y	z	U_iso*/U_eq
B1	0.4462 (3)	0.1262 (3)	0.0679 (3)	0.0532 (10)
C1	0.7708 (3)	0.2938 (3)	0.24399 (18)	0.0454 (8)
C2	0.8540 (3)	0.2801 (4)	0.3042 (2)	0.0760 (13)
H2	0.9264	0.2729	0.2923	0.091*
C3	0.8303 (4)	0.2772 (4)	0.3817 (2)	0.0881 (15)
H3	0.887	0.2698	0.4221	0.106*
C4	0.7244 (4)	0.2850 (4)	0.3997 (2)	0.0732 (12)
H4	0.7085	0.2809	0.4521	0.088*
C5	0.6422 (3)	0.2990 (4)	0.3407 (2)	0.0711 (12)
H5	0.57	0.3057	0.353	0.085*
C6	0.6645 (3)	0.3033 (3)	0.2629 (2)	0.0558 (9)
H6	0.6074	0.3127	0.2231	0.067*
C7	0.8321 (3)	0.4379 (3)	0.12130 (19)	0.0445 (8)
C8	0.8551 (4)	0.5149 (4)	0.1778 (3)	0.0886 (15)
H8	0.8539	0.4969	0.2309	0.106*
C9	0.8799 (5)	0.6187 (5)	0.1572 (3)	0.116 (2)
H9	0.8944	0.6704	0.1966	0.14*
C10	0.8837 (4)	0.6475 (4)	0.0815 (4)	0.0943 (16)
H10	0.9024	0.7178	0.0684	0.113*
C11	0.8599 (4)	0.5720 (4)	0.0243 (3)	0.0932 (15)
H11	0.8619	0.5909	−0.0285	0.112*
C12	0.8328 (4)	0.4686 (3)	0.0436 (2)	0.0732 (12)
H12	0.8147	0.4184	0.0036	0.088*
C13	0.9137 (3)	0.2202 (3)	0.12764 (18)	0.0462 (8)
C14	1.0189 (3)	0.2615 (3)	0.1331 (2)	0.0600 (10)
H14	1.0307	0.3341	0.1458	0.072*
C15	1.1067 (3)	0.1965 (5)	0.1199 (3)	0.0791 (13)
H15	1.1773	0.2254	0.1232	0.095*
C16	1.0903 (4)	0.0898 (5)	0.1019 (3)	0.0851 (14)
H16	1.1499	0.0462	0.0929	0.102*
C17	0.9869 (4)	0.0465 (4)	0.0970 (3)	0.0833 (14)
H17	0.9762	−0.0267	0.0856	0.1*
C18	0.8983 (3)	0.1118 (3)	0.1091 (2)	0.0654 (11)
H18	0.8278	0.0826	0.1048	0.078*
C19	0.4131 (2)	0.2237 (3)	0.1205 (2)	0.0499 (9)
C20	0.3890 (3)	0.2063 (3)	0.1978 (3)	0.0649 (11)
C21	0.3536 (3)	0.2925 (4)	0.2418 (3)	0.0792 (14)
H21	0.3389	0.2805	0.2938	0.095*
C22	0.3398 (4)	0.3942 (4)	0.2105 (4)	0.0868 (16)
C23	0.3665 (3)	0.4111 (4)	0.1346 (3)	0.0799 (14)
H23	0.3603	0.4805	0.1133	0.096*
C24	0.4023 (3)	0.3276 (3)	0.0892 (3)	0.0613 (10)
C25	0.4022 (4)	0.0969 (5)	0.2351 (3)	0.1026 (17)
H25A	0.4762	0.072	0.2326	0.154*
H25B	0.3519	0.0471	0.2074	0.154*
H25C	0.387	0.1013	0.2894	0.154*
C26	0.2944 (5)	0.4862 (5)	0.2583 (4)	0.139 (3)
H26A	0.3226	0.4794	0.3129	0.209*
H26B	0.2156	0.4823	0.2538	0.209*
H26C	0.3167	0.5546	0.2382	0.209*
C27	0.4303 (4)	0.3506 (4)	0.0065 (3)	0.0922 (15)
H27A	0.5088	0.3519	0.0059	0.138*
H27B	0.4003	0.4195	−0.0105	0.138*
H27C	0.3997	0.2949	−0.0285	0.138*
O1	0.69683 (17)	0.2649 (2)	0.08921 (13)	0.0520 (6)
O2	0.55104 (18)	0.1109 (2)	0.04987 (17)	0.0615 (7)
H2A	0.5885	0.1638	0.0642	0.092*
O3	0.3685 (2)	0.0561 (2)	0.0395 (2)	0.0792 (9)
H3A	0.3946	0.0134	0.0095	0.119*
P1	0.79424 (7)	0.30091 (7)	0.14123 (5)	0.0403 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.042 (2)	0.049 (2)	0.071 (3)	−0.0051 (18)	0.0146 (19)	−0.011 (2)
C1	0.0455 (19)	0.054 (2)	0.0379 (17)	−0.0065 (16)	0.0080 (14)	−0.0018 (15)
C2	0.054 (2)	0.133 (4)	0.041 (2)	0.003 (2)	0.0049 (17)	0.008 (2)
C3	0.077 (3)	0.147 (5)	0.040 (2)	0.011 (3)	0.002 (2)	0.015 (3)
C4	0.092 (3)	0.089 (3)	0.043 (2)	0.009 (3)	0.027 (2)	0.006 (2)
C5	0.068 (3)	0.096 (3)	0.054 (2)	0.008 (2)	0.028 (2)	0.008 (2)
C6	0.056 (2)	0.067 (2)	0.046 (2)	0.0010 (18)	0.0137 (16)	0.0003 (18)
C7	0.0386 (17)	0.054 (2)	0.0414 (18)	−0.0058 (15)	0.0071 (14)	−0.0007 (16)
C8	0.121 (4)	0.086 (3)	0.060 (3)	−0.052 (3)	0.016 (3)	−0.010 (2)
C9	0.169 (6)	0.092 (4)	0.091 (4)	−0.069 (4)	0.028 (4)	−0.024 (3)
C10	0.100 (4)	0.060 (3)	0.123 (5)	−0.026 (3)	0.013 (3)	0.012 (3)
C11	0.112 (4)	0.088 (4)	0.079 (3)	−0.014 (3)	0.002 (3)	0.031 (3)
C12	0.101 (3)	0.063 (3)	0.054 (2)	−0.013 (2)	0.001 (2)	0.009 (2)
C13	0.049 (2)	0.056 (2)	0.0354 (17)	−0.0041 (16)	0.0121 (14)	0.0053 (15)
C14	0.045 (2)	0.070 (3)	0.066 (2)	−0.0018 (18)	0.0091 (17)	0.008 (2)
C15	0.053 (2)	0.109 (4)	0.076 (3)	0.010 (3)	0.011 (2)	0.021 (3)
C16	0.083 (3)	0.106 (4)	0.069 (3)	0.039 (3)	0.024 (2)	0.011 (3)
C17	0.101 (4)	0.064 (3)	0.088 (3)	0.012 (3)	0.026 (3)	−0.006 (2)
C18	0.068 (3)	0.063 (3)	0.068 (3)	−0.006 (2)	0.022 (2)	−0.004 (2)
C19	0.0327 (17)	0.047 (2)	0.071 (2)	−0.0016 (14)	0.0082 (16)	−0.0158 (18)
C20	0.047 (2)	0.071 (3)	0.078 (3)	0.0016 (19)	0.0128 (19)	−0.014 (2)
C21	0.056 (2)	0.106 (4)	0.078 (3)	0.000 (2)	0.014 (2)	−0.037 (3)
C22	0.061 (3)	0.079 (4)	0.121 (4)	0.003 (2)	0.010 (3)	−0.051 (3)
C23	0.069 (3)	0.051 (2)	0.119 (4)	0.005 (2)	0.006 (3)	−0.023 (3)
C24	0.049 (2)	0.052 (2)	0.083 (3)	0.0019 (17)	0.0062 (19)	−0.016 (2)
C25	0.106 (4)	0.106 (4)	0.101 (4)	0.004 (3)	0.037 (3)	0.007 (3)
C26	0.121 (5)	0.121 (5)	0.180 (7)	0.017 (4)	0.034 (4)	−0.094 (5)
C27	0.092 (3)	0.078 (3)	0.108 (4)	0.008 (3)	0.019 (3)	0.013 (3)
O1	0.0442 (13)	0.0712 (16)	0.0411 (13)	−0.0167 (11)	0.0067 (10)	−0.0048 (11)
O2	0.0423 (14)	0.0562 (16)	0.0888 (19)	−0.0107 (11)	0.0206 (13)	−0.0316 (14)
O3	0.0438 (14)	0.0710 (19)	0.126 (3)	−0.0144 (13)	0.0257 (15)	−0.0464 (17)
P1	0.0377 (5)	0.0521 (5)	0.0318 (4)	−0.0119 (4)	0.0073 (3)	−0.0019 (4)

Geometric parameters (Å, º) top

B1—O3	1.339 (5)	C14—H14	0.93
B1—O2	1.359 (4)	C15—C16	1.362 (7)
B1—C19	1.574 (5)	C15—H15	0.93
C1—C6	1.374 (5)	C16—C17	1.368 (7)
C1—C2	1.379 (5)	C16—H16	0.93
C1—P1	1.798 (3)	C17—C18	1.381 (6)
C2—C3	1.377 (5)	C17—H17	0.93
C2—H2	0.93	C18—H18	0.93
C3—C4	1.362 (6)	C19—C24	1.388 (5)
C3—H3	0.93	C19—C20	1.391 (5)
C4—C5	1.359 (6)	C20—C21	1.393 (6)
C4—H4	0.93	C20—C25	1.494 (6)
C5—C6	1.375 (5)	C21—C22	1.368 (7)
C5—H5	0.93	C21—H21	0.93
C6—H6	0.93	C22—C23	1.375 (7)
C7—C8	1.360 (5)	C22—C26	1.531 (6)
C7—C12	1.374 (5)	C23—C24	1.383 (6)
C7—P1	1.794 (3)	C23—H23	0.93
C8—C9	1.370 (7)	C24—C27	1.505 (6)
C8—H8	0.93	C25—H25A	0.96
C9—C10	1.339 (7)	C25—H25B	0.96
C9—H9	0.93	C25—H25C	0.96
C10—C11	1.356 (7)	C26—H26A	0.96
C10—H10	0.93	C26—H26B	0.96
C11—C12	1.366 (6)	C26—H26C	0.96
C11—H11	0.93	C27—H27A	0.96
C12—H12	0.93	C27—H27B	0.96
C13—C14	1.377 (5)	C27—H27C	0.96
C13—C18	1.383 (5)	O1—P1	1.479 (2)
C13—P1	1.801 (3)	O2—H2A	0.82
C14—C15	1.376 (6)	O3—H3A	0.82

O3—B1—O2	118.7 (3)	C16—C17—C18	119.7 (4)
O3—B1—C19	119.0 (3)	C16—C17—H17	120.1
O2—B1—C19	122.3 (3)	C18—C17—H17	120.1
C6—C1—C2	118.8 (3)	C17—C18—C13	120.5 (4)
C6—C1—P1	117.9 (3)	C17—C18—H18	119.8
C2—C1—P1	123.3 (3)	C13—C18—H18	119.8
C3—C2—C1	120.2 (4)	C24—C19—C20	118.8 (3)
C3—C2—H2	119.9	C24—C19—B1	120.6 (3)
C1—C2—H2	119.9	C20—C19—B1	120.5 (3)
C4—C3—C2	120.5 (4)	C19—C20—C21	119.7 (4)
C4—C3—H3	119.8	C19—C20—C25	121.1 (4)
C2—C3—H3	119.8	C21—C20—C25	119.2 (4)
C5—C4—C3	119.6 (4)	C22—C21—C20	121.6 (5)
C5—C4—H4	120.2	C22—C21—H21	119.2
C3—C4—H4	120.2	C20—C21—H21	119.2
C4—C5—C6	120.7 (4)	C21—C22—C23	118.2 (4)
C4—C5—H5	119.6	C21—C22—C26	120.7 (6)
C6—C5—H5	119.6	C23—C22—C26	121.1 (6)
C1—C6—C5	120.2 (4)	C22—C23—C24	121.8 (5)
C1—C6—H6	119.9	C22—C23—H23	119.1
C5—C6—H6	119.9	C24—C23—H23	119.1
C8—C7—C12	117.7 (4)	C23—C24—C19	119.9 (4)
C8—C7—P1	124.3 (3)	C23—C24—C27	119.6 (4)
C12—C7—P1	117.9 (3)	C19—C24—C27	120.6 (4)
C7—C8—C9	120.5 (4)	C20—C25—H25A	109.5
C7—C8—H8	119.8	C20—C25—H25B	109.5
C9—C8—H8	119.8	H25A—C25—H25B	109.5
C10—C9—C8	121.6 (5)	C20—C25—H25C	109.5
C10—C9—H9	119.2	H25A—C25—H25C	109.5
C8—C9—H9	119.2	H25B—C25—H25C	109.5
C9—C10—C11	118.7 (5)	C22—C26—H26A	109.5
C9—C10—H10	120.7	C22—C26—H26B	109.5
C11—C10—H10	120.7	H26A—C26—H26B	109.5
C10—C11—C12	120.7 (5)	C22—C26—H26C	109.5
C10—C11—H11	119.7	H26A—C26—H26C	109.5
C12—C11—H11	119.7	H26B—C26—H26C	109.5
C11—C12—C7	120.8 (4)	C24—C27—H27A	109.5
C11—C12—H12	119.6	C24—C27—H27B	109.5
C7—C12—H12	119.6	H27A—C27—H27B	109.5
C14—C13—C18	118.6 (3)	C24—C27—H27C	109.5
C14—C13—P1	123.4 (3)	H27A—C27—H27C	109.5
C18—C13—P1	118.1 (3)	H27B—C27—H27C	109.5
C15—C14—C13	120.8 (4)	B1—O2—H2A	109.5
C15—C14—H14	119.6	B1—O3—H3A	109.5
C13—C14—H14	119.6	O1—P1—C7	112.18 (15)
C16—C15—C14	120.0 (4)	O1—P1—C1	111.68 (14)
C16—C15—H15	120	C7—P1—C1	107.33 (15)
C14—C15—H15	120	O1—P1—C13	111.86 (15)
C15—C16—C17	120.4 (4)	C7—P1—C13	105.64 (15)
C15—C16—H16	119.8	C1—P1—C13	107.82 (15)
C17—C16—H16	119.8

C6—C1—C2—C3	−0.6 (7)	B1—C19—C20—C25	4.8 (6)
P1—C1—C2—C3	178.9 (4)	C19—C20—C21—C22	1.2 (6)
C1—C2—C3—C4	1.6 (8)	C25—C20—C21—C22	−179.8 (4)
C2—C3—C4—C5	−1.9 (8)	C20—C21—C22—C23	−2.8 (7)
C3—C4—C5—C6	1.2 (7)	C20—C21—C22—C26	176.5 (4)
C2—C1—C6—C5	−0.1 (6)	C21—C22—C23—C24	2.5 (7)
P1—C1—C6—C5	−179.6 (3)	C26—C22—C23—C24	−176.7 (4)
C4—C5—C6—C1	−0.2 (6)	C22—C23—C24—C19	−0.7 (6)
C12—C7—C8—C9	−1.2 (7)	C22—C23—C24—C27	179.9 (4)
P1—C7—C8—C9	−177.9 (4)	C20—C19—C24—C23	−1.0 (5)
C7—C8—C9—C10	−0.8 (10)	B1—C19—C24—C23	175.9 (3)
C8—C9—C10—C11	1.5 (10)	C20—C19—C24—C27	178.4 (4)
C9—C10—C11—C12	−0.2 (9)	B1—C19—C24—C27	−4.7 (5)
C10—C11—C12—C7	−1.8 (8)	C8—C7—P1—O1	132.5 (4)
C8—C7—C12—C11	2.5 (7)	C12—C7—P1—O1	−44.2 (3)
P1—C7—C12—C11	179.4 (4)	C8—C7—P1—C1	9.4 (4)
C18—C13—C14—C15	0.4 (5)	C12—C7—P1—C1	−167.3 (3)
P1—C13—C14—C15	−178.1 (3)	C8—C7—P1—C13	−105.4 (4)
C13—C14—C15—C16	−0.6 (6)	C12—C7—P1—C13	77.9 (3)
C14—C15—C16—C17	−0.2 (7)	C6—C1—P1—O1	−27.1 (3)
C15—C16—C17—C18	1.1 (7)	C2—C1—P1—O1	153.4 (3)
C16—C17—C18—C13	−1.3 (7)	C6—C1—P1—C7	96.2 (3)
C14—C13—C18—C17	0.5 (6)	C2—C1—P1—C7	−83.3 (4)
P1—C13—C18—C17	179.1 (3)	C6—C1—P1—C13	−150.4 (3)
O3—B1—C19—C24	−103.4 (5)	C2—C1—P1—C13	30.1 (4)
O2—B1—C19—C24	76.2 (5)	C14—C13—P1—O1	145.3 (3)
O3—B1—C19—C20	73.4 (5)	C18—C13—P1—O1	−33.3 (3)
O2—B1—C19—C20	−106.9 (4)	C14—C13—P1—C7	23.0 (3)
C24—C19—C20—C21	0.7 (5)	C18—C13—P1—C7	−155.6 (3)
B1—C19—C20—C21	−176.2 (3)	C14—C13—P1—C1	−91.6 (3)
C24—C19—C20—C25	−178.3 (4)	C18—C13—P1—C1	89.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C19–C24 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.84	2.645 (3)	168
O3—H3A···O2ⁱ	0.82	1.99	2.795 (4)	169
C4—H4···O1ⁱⁱ	0.93	2.41	3.326 (4)	167
C6—H6···Cg4	0.93	2.88	3.728 (4)	152
C15—H15···Cg4ⁱⁱⁱ	0.93	2.69	3.602 (5)	168

Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₉H₁₃BO₂·C₁₈H₁₅OP
M_r	442.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	12.218 (4), 12.339 (4), 16.983 (5)
β (°)	95.651 (5)
V (Å³)	2548.0 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.52 × 0.45 × 0.42

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.934, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	23787, 4486, 3727
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.186, 1.19
No. of reflections	4486
No. of parameters	294
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.32

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C19–C24 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.84	2.645 (3)	168
O3—H3A···O2ⁱ	0.82	1.99	2.795 (4)	169
C4—H4···O1ⁱⁱ	0.93	2.41	3.326 (4)	167
C6—H6···Cg4	0.93	2.88	3.728 (4)	152
C15—H15···Cg4ⁱⁱⁱ	0.93	2.69	3.602 (5)	168

Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+1/2, z+1/2; (iii) x+1, y, z.

Acknowledgements

This work was supported by the National University Research Council (CNCS) of Romania (project TE295/2010). We thank Dr Albert Soran for the crystallographic measurements and data refinement.

References

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