(2,4,6-Trimethyl-phen-yl)boronic acid-triphenyl-phosphine oxide (1/1).

In the crystal structure of the title compound, C(9)H(13)BO(2)·C(18)H(15)OP, there are O-H⋯O hydrogen bonds between the O atom of triphenyl-phosphine oxide and one hy-droxy group of the boronic acid. Boronic acid mol-ecules form inversion-related hydrogen-bonded dimers in an R(2) (2)(8) motif. The structure is consolidated by inter-molecular C-H⋯O bonds and C-H⋯π inter-actions.

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 = 442.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.186

S = 1.19

4486 reflections

294 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.32 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051609/pk2368sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811051609/pk2368Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H13BO2·C18H15OP	F(000) = 936
Mr = 442.27	Dx = 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

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

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(Fo2) + (0.0654P)2 + 1.8657P] where P = (Fo2 + 2Fc2)/3
4486 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.32 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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .