Literature DB >> 21202827

A new polymorph of dimesitylborinic acid.

Matthias Kuhlmann1, Thomas Baumgartner, Masood Parvez.   

Abstract

A new polymorph of dimesitylborinic acid (or hydroxy-dimesitylborane), C(18)H(23)BO, showcasing different crystal packing and symmetry, complements the previously reported polymorph [Weese, Bartlett, Murray, Olmstead & Power (1987 ▶). Inorg. Chem.26, 2409-2413; Entwistle, Batsanov & Marder (2007 ▶). Acta Cryst. E63, o2639-o2641]. The structure of the title compound contains only one mol-ecule in the asymmetric unit, and no O-H⋯O inter-actions are observed. However, mol-ecules are linked by weak inter-molecuar O-H⋯π(arene) inter-actions to form centrosymmetric dimers.

Entities:  

Year:  2008        PMID： 21202827      PMCID： PMC2961869          DOI： 10.1107/S1600536808015638

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


Related literature

For related literature, see: Cornet et al. (2003 ▶); Entwistle et al. (2007 ▶); Fraenk et al. (2001 ▶); Kuhlmann et al. (2008 ▶); Weese et al. (1987 ▶).

Experimental

Crystal data

C18H23BO M = 266.17 Monoclinic, a = 8.942 (4) Å b = 8.801 (2) Å c = 19.947 (8) Å β = 97.800 (16)° V = 1555.3 (10) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 173 (2) K 0.32 × 0.24 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.979, T max = 0.992 6119 measured reflections 3542 independent reflections 2728 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.134 S = 0.91 3542 reflections 188 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.26 e Å−3 Δρmin = −0.19 e Å−3 Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015638/om2237sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015638/om2237Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H23BOF000 = 576
Mr = 266.17Dx = 1.137 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6119 reflections
a = 8.942 (4) Åθ = 3.3–27.5º
b = 8.801 (2) ŵ = 0.07 mm−1
c = 19.947 (8) ÅT = 173 (2) K
β = 97.800 (16)ºBlock, yellow
V = 1555.3 (10) Å30.32 × 0.24 × 0.12 mm
Z = 4
Nonius KappaCCD diffractometer3542 independent reflections
Radiation source: fine-focus sealed tube2728 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 173(2) Kθmax = 27.5º
ω and φ scansθmin = 3.3º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)h = −11→11
Tmin = 0.979, Tmax = 0.992k = −11→11
6119 measured reflectionsl = −25→25
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134  w = 1/[σ2(Fo2) + (0.072P)2 + 0.71P] where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
3542 reflectionsΔρmax = 0.26 e Å−3
188 parametersΔρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/UeqOcc. (<1)
O10.11790 (13)−0.31566 (13)−0.00945 (5)0.0401 (3)
H10.076 (2)−0.251 (2)−0.0366 (10)0.048*
B10.08930 (17)−0.28800 (17)0.05445 (8)0.0269 (3)
C20.17055 (15)−0.39649 (14)0.11108 (6)0.0255 (3)
C30.32785 (15)−0.42311 (15)0.11607 (7)0.0278 (3)
C40.39909 (15)−0.51699 (15)0.16679 (7)0.0309 (3)
H40.5049−0.53240.16980.037*
C50.32018 (16)−0.58890 (15)0.21314 (7)0.0316 (3)
C60.16562 (16)−0.56426 (15)0.20763 (7)0.0310 (3)
H60.1095−0.61380.23840.037*
C70.09009 (15)−0.46888 (15)0.15823 (7)0.0276 (3)
C80.42383 (17)−0.35135 (18)0.06779 (8)0.0374 (4)
H8A0.5308−0.36330.08570.045*
H8B0.3995−0.24300.06280.045*
H8C0.4034−0.40130.02360.045*
C90.3997 (2)−0.68880 (19)0.26809 (8)0.0446 (4)
H9A0.5077−0.69260.26410.067*0.50
H9B0.3574−0.79160.26360.067*0.50
H9C0.3858−0.64720.31240.067*0.50
H9D0.3262−0.72830.29600.067*0.50
H9E0.4765−0.62940.29650.067*0.50
H9F0.4481−0.77370.24760.067*0.50
C10−0.07788 (16)−0.44837 (18)0.15670 (8)0.0364 (3)
H10A−0.1137−0.51440.19070.044*
H10B−0.1295−0.47520.11170.044*
H10C−0.0995−0.34220.16660.044*
C11−0.02005 (15)−0.15448 (14)0.06966 (7)0.0265 (3)
C12−0.17091 (15)−0.15062 (15)0.03816 (7)0.0286 (3)
C13−0.27017 (16)−0.04211 (16)0.05784 (7)0.0320 (3)
H13−0.3721−0.04200.03690.038*
C14−0.22404 (17)0.06574 (16)0.10723 (7)0.0337 (3)
C15−0.07360 (17)0.06623 (15)0.13554 (7)0.0330 (3)
H15−0.03920.14240.16770.040*
C160.02899 (16)−0.04183 (15)0.11824 (7)0.0292 (3)
C17−0.23031 (17)−0.26522 (18)−0.01535 (8)0.0367 (3)
H17A−0.3408−0.2611−0.02280.044*
H17B−0.1976−0.3674−0.00020.044*
H17C−0.1910−0.2415−0.05770.044*
C18−0.3345 (2)0.17870 (19)0.12935 (10)0.0471 (4)
H18A−0.43470.16100.10400.071*0.50
H18B−0.30130.28210.12060.071*0.50
H18C−0.33920.16640.17780.071*0.50
H18D−0.28210.24530.16430.071*0.50
H18E−0.41550.12420.14770.071*0.50
H18F−0.37760.23990.09040.071*0.50
C190.18953 (18)−0.03689 (18)0.15248 (8)0.0405 (4)
H19A0.20800.06000.17630.049*
H19B0.2584−0.04680.11850.049*
H19C0.2068−0.12070.18500.049*
U11U22U33U12U13U23
O10.0500 (7)0.0443 (6)0.0276 (5)0.0133 (5)0.0115 (5)0.0046 (4)
B10.0270 (7)0.0273 (7)0.0274 (8)−0.0023 (6)0.0068 (6)−0.0004 (6)
C20.0284 (7)0.0225 (6)0.0259 (6)0.0005 (5)0.0056 (5)−0.0035 (5)
C30.0298 (7)0.0247 (6)0.0298 (7)−0.0015 (5)0.0066 (5)−0.0061 (5)
C40.0276 (7)0.0282 (7)0.0359 (8)0.0022 (5)0.0012 (6)−0.0078 (5)
C50.0378 (8)0.0267 (7)0.0286 (7)0.0017 (6)−0.0012 (6)−0.0035 (5)
C60.0381 (8)0.0282 (7)0.0270 (7)−0.0007 (6)0.0059 (6)0.0002 (5)
C70.0309 (7)0.0264 (6)0.0260 (6)0.0010 (5)0.0060 (5)−0.0030 (5)
C80.0321 (7)0.0411 (8)0.0409 (8)−0.0018 (6)0.0119 (6)−0.0009 (6)
C90.0470 (9)0.0417 (9)0.0418 (9)0.0063 (7)−0.0054 (7)0.0067 (7)
C100.0331 (8)0.0413 (8)0.0368 (8)0.0021 (6)0.0124 (6)0.0079 (6)
C110.0302 (7)0.0247 (6)0.0251 (6)0.0009 (5)0.0055 (5)0.0032 (5)
C120.0308 (7)0.0260 (6)0.0290 (7)−0.0008 (5)0.0042 (5)0.0032 (5)
C130.0289 (7)0.0315 (7)0.0358 (8)0.0019 (5)0.0048 (6)0.0051 (6)
C140.0380 (8)0.0271 (7)0.0380 (8)0.0059 (6)0.0122 (6)0.0043 (6)
C150.0431 (8)0.0249 (7)0.0313 (7)0.0009 (6)0.0057 (6)−0.0032 (5)
C160.0341 (7)0.0255 (6)0.0278 (7)0.0004 (5)0.0032 (6)0.0029 (5)
C170.0350 (8)0.0383 (8)0.0360 (8)−0.0045 (6)0.0012 (6)−0.0047 (6)
C180.0457 (9)0.0391 (9)0.0590 (11)0.0129 (7)0.0168 (8)−0.0020 (7)
C190.0391 (8)0.0373 (8)0.0424 (8)0.0021 (6)−0.0044 (7)−0.0085 (7)
O1—B11.3556 (19)C10—H10B0.9800
O1—H10.84 (2)C10—H10C0.9800
B1—C21.579 (2)C11—C121.409 (2)
B1—C111.584 (2)C11—C161.4139 (19)
C2—C71.4113 (19)C12—C131.3958 (19)
C2—C31.4161 (19)C12—C171.512 (2)
C3—C41.3918 (19)C13—C141.390 (2)
C3—C81.512 (2)C13—H130.9500
C4—C51.389 (2)C14—C151.386 (2)
C4—H40.9500C14—C181.509 (2)
C5—C61.388 (2)C15—C161.397 (2)
C5—C91.506 (2)C15—H150.9500
C6—C71.3968 (19)C16—C191.504 (2)
C6—H60.9500C17—H17A0.9800
C7—C101.509 (2)C17—H17B0.9800
C8—H8A0.9800C17—H17C0.9800
C8—H8B0.9800C18—H18A0.9800
C8—H8C0.9800C18—H18B0.9800
C9—H9A0.9800C18—H18C0.9800
C9—H9B0.9800C18—H18D0.9800
C9—H9C0.9800C18—H18E0.9800
C9—H9D0.9800C18—H18F0.9800
C9—H9E0.9800C19—H19A0.9800
C9—H9F0.9800C19—H19B0.9800
C10—H10A0.9800C19—H19C0.9800
B1—O1—H1111.0 (13)H10A—C10—H10C109.5
O1—B1—C2115.90 (12)H10B—C10—H10C109.5
O1—B1—C11120.89 (12)C12—C11—C16118.54 (12)
C2—B1—C11123.21 (12)C12—C11—B1120.73 (12)
C7—C2—C3118.02 (12)C16—C11—B1120.62 (12)
C7—C2—B1121.54 (12)C13—C12—C11119.86 (13)
C3—C2—B1120.43 (12)C13—C12—C17118.63 (13)
C4—C3—C2120.10 (12)C11—C12—C17121.47 (12)
C4—C3—C8117.87 (13)C14—C13—C12121.86 (13)
C2—C3—C8122.03 (13)C14—C13—H13119.1
C5—C4—C3122.04 (13)C12—C13—H13119.1
C5—C4—H4119.0C15—C14—C13117.97 (13)
C3—C4—H4119.0C15—C14—C18121.08 (14)
C6—C5—C4117.78 (13)C13—C14—C18120.95 (14)
C6—C5—C9121.02 (13)C14—C15—C16122.05 (13)
C4—C5—C9121.20 (14)C14—C15—H15119.0
C5—C6—C7122.04 (13)C16—C15—H15119.0
C5—C6—H6119.0C15—C16—C11119.59 (13)
C7—C6—H6119.0C15—C16—C19119.10 (13)
C6—C7—C2120.00 (13)C11—C16—C19121.30 (12)
C6—C7—C10118.09 (12)C12—C17—H17A109.5
C2—C7—C10121.91 (12)C12—C17—H17B109.5
C3—C8—H8A109.5H17A—C17—H17B109.5
C3—C8—H8B109.5C12—C17—H17C109.5
H8A—C8—H8B109.5H17A—C17—H17C109.5
C3—C8—H8C109.5H17B—C17—H17C109.5
H8A—C8—H8C109.5C14—C18—H18A109.5
H8B—C8—H8C109.5C14—C18—H18B109.5
C5—C9—H9A109.5H18A—C18—H18B109.5
C5—C9—H9B109.5C14—C18—H18C109.5
H9A—C9—H9B109.5H18A—C18—H18C109.5
C5—C9—H9C109.5H18B—C18—H18C109.5
H9A—C9—H9C109.5C14—C18—H18D109.5
H9B—C9—H9C109.5H18A—C18—H18D141.1
C5—C9—H9D109.5H18B—C18—H18D56.3
H9A—C9—H9D141.1H18C—C18—H18D56.3
H9B—C9—H9D56.3C14—C18—H18E109.5
H9C—C9—H9D56.3H18A—C18—H18E56.3
C5—C9—H9E109.5H18B—C18—H18E141.1
H9A—C9—H9E56.3H18C—C18—H18E56.3
H9B—C9—H9E141.1H18D—C18—H18E109.5
H9C—C9—H9E56.3C14—C18—H18F109.5
H9D—C9—H9E109.5H18A—C18—H18F56.3
C5—C9—H9F109.5H18B—C18—H18F56.3
H9A—C9—H9F56.3H18C—C18—H18F141.1
H9B—C9—H9F56.3H18D—C18—H18F109.5
H9C—C9—H9F141.1H18E—C18—H18F109.5
H9D—C9—H9F109.5C16—C19—H19A109.5
H9E—C9—H9F109.5C16—C19—H19B109.5
C7—C10—H10A109.5H19A—C19—H19B109.5
C7—C10—H10B109.5C16—C19—H19C109.5
H10A—C10—H10B109.5H19A—C19—H19C109.5
C7—C10—H10C109.5H19B—C19—H19C109.5
O1—B1—C2—C7−130.25 (14)O1—B1—C11—C1258.47 (18)
C11—B1—C2—C749.51 (18)C2—B1—C11—C12−121.28 (14)
O1—B1—C2—C350.12 (18)O1—B1—C11—C16−125.45 (15)
C11—B1—C2—C3−130.12 (14)C2—B1—C11—C1654.80 (18)
C7—C2—C3—C4−0.66 (18)C16—C11—C12—C13−3.41 (19)
B1—C2—C3—C4178.98 (12)B1—C11—C12—C13172.75 (12)
C7—C2—C3—C8179.76 (12)C16—C11—C12—C17178.63 (13)
B1—C2—C3—C8−0.60 (19)B1—C11—C12—C17−5.21 (19)
C2—C3—C4—C50.9 (2)C11—C12—C13—C141.3 (2)
C8—C3—C4—C5−179.46 (13)C17—C12—C13—C14179.29 (13)
C3—C4—C5—C6−0.1 (2)C12—C13—C14—C152.0 (2)
C3—C4—C5—C9−179.37 (13)C12—C13—C14—C18−177.96 (14)
C4—C5—C6—C7−1.0 (2)C13—C14—C15—C16−3.1 (2)
C9—C5—C6—C7178.25 (13)C18—C14—C15—C16176.82 (14)
C5—C6—C7—C21.3 (2)C14—C15—C16—C111.0 (2)
C5—C6—C7—C10−179.50 (13)C14—C15—C16—C19−178.29 (14)
C3—C2—C7—C6−0.42 (18)C12—C11—C16—C152.32 (19)
B1—C2—C7—C6179.94 (12)B1—C11—C16—C15−173.84 (12)
C3—C2—C7—C10−179.59 (12)C12—C11—C16—C19−178.42 (13)
B1—C2—C7—C100.77 (19)B1—C11—C16—C195.4 (2)
D—H···AD—HH···AD···AD—H···A
O1—H1···Cgi0.84 (2)2.83 (2)3.523 (2)141 (2)
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 phenyl ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯Cgi0.84 (2)2.83 (2)3.523 (2)141 (2)

Symmetry code: (i) .

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