The title compound, C10H11BO3, may be developed as a potent boron neutron capture therapy (BNCT) drug for hepatoma treatment. The compound was obtained as transparent rectangular plate crystals. Intermolecular hydrogen bonds and π–π interactions help stabilize the crystal structure.
Supporting information
CCDC reference: 253024
Key indicators
- Single-crystal X-ray study
- T = 294 K
- R factor = 0.034
- wR factor = 0.102
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
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PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
3-(4-dihydroxyborylphenyl)cyclobutanone
top
Crystal data top
| C10H11BO3 | F(000) = 400 |
| Mr = 190.00 | Dx = 1.353 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.4645 (11) Å | Cell parameters from 5680 reflections |
| b = 9.8317 (9) Å | θ = 2.0–28.0° |
| c = 8.3674 (8) Å | µ = 0.10 mm−1 |
| β = 98.551 (2)° | T = 294 K |
| V = 932.65 (15) Å3 | Rectangular plate, colourless |
| Z = 4 | 0.15 × 0.10 × 0.05 mm |
Data collection top
Bruker SMART CCD area-detector
diffractometer | 1915 independent reflections |
| Radiation source: fine-focus sealed tube | 1198 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.076 |
| φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: psi scan
(SHELXTL; Bruker, 2000) | h = −14→12 |
| Tmin = 0.927, Tmax = 0.993 | k = −11→12 |
| 5481 measured reflections | l = −10→10 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.102 | All H-atom parameters refined |
| S = 0.96 | w = 1/[σ2(Fo2)(0.1P)2]
where P = (Fo2 + 2Fc2)/3 |
| 1915 reflections | (Δ/σ)max < 0.001 |
| 171 parameters | Δρmax = 0.15 e Å−3 |
| 0 restraints | Δρmin = −0.13 e Å−3 |
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 | Uiso*/Ueq | |
| O1 | 0.96582 (10) | −0.12063 (10) | 0.17237 (13) | 0.0421 (3) | |
| O2 | 0.97563 (10) | 0.11504 (11) | 0.14493 (13) | 0.0439 (3) | |
| O3 | 0.51464 (13) | −0.17211 (14) | 0.97457 (18) | 0.0791 (5) | |
| C1 | 0.86396 (11) | 0.01649 (13) | 0.36538 (15) | 0.0306 (3) | |
| C2 | 0.81769 (12) | 0.13894 (14) | 0.41091 (17) | 0.0341 (3) | |
| C3 | 0.74740 (12) | 0.14610 (15) | 0.53204 (16) | 0.0332 (3) | |
| C4 | 0.72100 (11) | 0.03049 (13) | 0.61429 (17) | 0.0316 (3) | |
| C5 | 0.76642 (13) | −0.09298 (15) | 0.56952 (18) | 0.0402 (4) | |
| C6 | 0.83532 (13) | −0.09938 (15) | 0.44819 (18) | 0.0389 (4) | |
| C7 | 0.64392 (12) | 0.03936 (15) | 0.74417 (17) | 0.0352 (3) | |
| C8 | 0.68371 (15) | −0.03663 (19) | 0.9057 (2) | 0.0457 (4) | |
| C9 | 0.56397 (14) | −0.10426 (15) | 0.88585 (19) | 0.0471 (4) | |
| C10 | 0.52803 (15) | −0.0457 (2) | 0.7210 (2) | 0.0506 (5) | |
| B | 0.93881 (14) | 0.00511 (15) | 0.22510 (19) | 0.0316 (4) | |
| H1O | 0.997 (2) | −0.122 (2) | 0.082 (3) | 0.082 (7)* | |
| H2O | 0.9727 (15) | 0.185 (2) | 0.188 (2) | 0.055 (6)* | |
| H2 | 0.8279 (14) | 0.2214 (17) | 0.3561 (19) | 0.048 (4)* | |
| H3 | 0.7165 (13) | 0.2321 (17) | 0.5588 (18) | 0.046 (4)* | |
| H5 | 0.7478 (14) | −0.1745 (16) | 0.626 (2) | 0.050 (5)* | |
| H6 | 0.8603 (14) | −0.1840 (17) | 0.4195 (19) | 0.048 (4)* | |
| H7 | 0.6289 (14) | 0.1335 (16) | 0.758 (2) | 0.055 (5)* | |
| H8A | 0.6992 (16) | 0.0169 (18) | 1.004 (3) | 0.069 (6)* | |
| H8B | 0.7483 (17) | −0.1051 (19) | 0.898 (2) | 0.070 (5)* | |
| H10B | 0.5274 (19) | −0.112 (2) | 0.638 (2) | 0.081 (6)* | |
| H10A | 0.4530 (19) | 0.0064 (19) | 0.710 (3) | 0.084 (7)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0560 (7) | 0.0335 (6) | 0.0429 (6) | 0.0020 (4) | 0.0271 (5) | −0.0007 (4) |
| O2 | 0.0607 (7) | 0.0324 (6) | 0.0457 (6) | −0.0024 (5) | 0.0308 (5) | −0.0011 (5) |
| O3 | 0.0899 (10) | 0.0615 (9) | 0.0981 (11) | −0.0106 (7) | 0.0546 (9) | 0.0183 (7) |
| C1 | 0.0291 (7) | 0.0328 (7) | 0.0306 (7) | −0.0003 (5) | 0.0071 (6) | −0.0006 (5) |
| C2 | 0.0378 (8) | 0.0309 (8) | 0.0353 (8) | −0.0017 (6) | 0.0106 (6) | 0.0026 (6) |
| C3 | 0.0339 (8) | 0.0305 (8) | 0.0370 (8) | 0.0015 (5) | 0.0107 (6) | −0.0015 (6) |
| C4 | 0.0290 (7) | 0.0353 (8) | 0.0317 (7) | −0.0021 (5) | 0.0080 (6) | 0.0000 (6) |
| C5 | 0.0470 (9) | 0.0308 (8) | 0.0473 (9) | 0.0014 (6) | 0.0215 (7) | 0.0062 (6) |
| C6 | 0.0439 (9) | 0.0297 (8) | 0.0476 (9) | 0.0045 (6) | 0.0219 (7) | 0.0022 (6) |
| C7 | 0.0354 (8) | 0.0362 (8) | 0.0364 (8) | −0.0017 (6) | 0.0131 (6) | −0.0008 (6) |
| C8 | 0.0453 (10) | 0.0558 (10) | 0.0378 (9) | 0.0042 (8) | 0.0122 (7) | 0.0030 (7) |
| C9 | 0.0554 (10) | 0.0370 (9) | 0.0559 (10) | −0.0021 (7) | 0.0310 (8) | −0.0023 (7) |
| C10 | 0.0369 (9) | 0.0737 (12) | 0.0450 (10) | −0.0100 (8) | 0.0182 (8) | −0.0060 (9) |
| B | 0.0324 (8) | 0.0304 (8) | 0.0330 (8) | −0.0006 (6) | 0.0082 (7) | 0.0025 (6) |
Geometric parameters (Å, º) top
| O1—B | 1.364 (2) | C4—C7 | 1.5017 (19) |
| O1—H1O | 0.88 (2) | C5—C6 | 1.377 (2) |
| O2—B | 1.371 (2) | C5—H5 | 0.971 (17) |
| O2—H2O | 0.78 (2) | C6—H6 | 0.924 (17) |
| O3—C9 | 1.200 (2) | C7—C8 | 1.553 (2) |
| C1—C2 | 1.3914 (19) | C7—C10 | 1.557 (2) |
| C1—C6 | 1.3976 (19) | C7—H7 | 0.952 (16) |
| C1—B | 1.558 (2) | C8—C9 | 1.512 (2) |
| C2—C3 | 1.3873 (19) | C8—H8A | 0.97 (2) |
| C2—H2 | 0.948 (16) | C8—H8B | 1.009 (19) |
| C3—C4 | 1.3854 (19) | C9—C10 | 1.495 (2) |
| C3—H3 | 0.957 (16) | C10—H10B | 0.95 (2) |
| C4—C5 | 1.3939 (19) | C10—H10A | 0.99 (2) |
| | | |
| B—O1—H1O | 115.3 (14) | C8—C7—C10 | 89.13 (12) |
| B—O2—H2O | 115.7 (13) | C4—C7—H7 | 106.5 (11) |
| C2—C1—C6 | 116.25 (13) | C8—C7—H7 | 113.2 (10) |
| C2—C1—B | 122.9 (1) | C10—C7—H7 | 111.8 (10) |
| C6—C1—B | 120.8 (1) | C9—C8—C7 | 88.36 (12) |
| C3—C2—C1 | 122.04 (13) | C9—C8—H8A | 112.4 (11) |
| C3—C2—H2 | 115.9 (10) | C7—C8—H8A | 118.0 (11) |
| C1—C2—H2 | 121.9 (10) | C9—C8—H8B | 111.2 (10) |
| C4—C3—C2 | 120.99 (13) | C7—C8—H8B | 112.9 (11) |
| C4—C3—H3 | 119.6 (9) | H8A—C8—H8B | 111.8 (16) |
| C2—C3—H3 | 119.5 (9) | O3—C9—C10 | 134.0 (2) |
| C3—C4—C5 | 117.59 (13) | O3—C9—C8 | 132.8 (2) |
| C3—C4—C7 | 120.49 (12) | C10—C9—C8 | 93.05 (12) |
| C5—C4—C7 | 121.91 (13) | C9—C10—C7 | 88.80 (12) |
| C6—C5—C4 | 121.06 (13) | C9—C10—H10B | 112.2 (12) |
| C6—C5—H5 | 121.0 (10) | C7—C10—H10B | 111.9 (13) |
| C4—C5—H5 | 118.0 (10) | C9—C10—H10A | 113.7 (13) |
| C5—C6—C1 | 122.07 (14) | C7—C10—H10A | 116.5 (12) |
| C5—C6—H6 | 117.8 (10) | H10B—C10—H10A | 111.9 (18) |
| C1—C6—H6 | 120.1 (10) | O1—B—O2 | 117.1 (1) |
| C4—C7—C8 | 118.28 (12) | O1—B—C1 | 119.1 (1) |
| C4—C7—C10 | 117.50 (13) | O2—B—C1 | 123.8 (1) |
| | | |
| C6—C1—C2—C3 | 0.2 (2) | C5—C4—C7—C10 | −57.99 (19) |
| B—C1—C2—C3 | 177.44 (12) | C4—C7—C8—C9 | −127.08 (13) |
| C1—C2—C3—C4 | 0.5 (2) | C10—C7—C8—C9 | −6.00 (13) |
| C2—C3—C4—C5 | −0.7 (2) | C7—C8—C9—O3 | −169.58 (19) |
| C2—C3—C4—C7 | −179.45 (12) | C7—C8—C9—C10 | 6.25 (14) |
| C3—C4—C5—C6 | 0.2 (2) | O3—C9—C10—C7 | 169.5 (2) |
| C7—C4—C5—C6 | 178.88 (14) | C8—C9—C10—C7 | −6.23 (13) |
| C4—C5—C6—C1 | 0.6 (2) | C4—C7—C10—C9 | 127.83 (14) |
| C2—C1—C6—C5 | −0.8 (2) | C8—C7—C10—C9 | 6.06 (13) |
| B—C1—C6—C5 | −178.07 (13) | C2—C1—B—O1 | −170.26 (13) |
| C3—C4—C7—C8 | −134.23 (15) | C6—C1—B—O1 | 6.8 (2) |
| C5—C4—C7—C8 | 47.12 (19) | C2—C1—B—O2 | 6.7 (2) |
| C3—C4—C7—C10 | 120.65 (16) | C6—C1—B—O2 | −176.20 (14) |
Some related bond distances (Å) to B atom of boronated compounds. top| Longer (L), Shorter (S) or Equal (E) as compared with this (T) work. |
| Compound | B—C | | B—O | (l) | B—O | (s) |
| BPCBa | 1.558 (2) | (T) | 1.3713 (18) | (T) | 1.3637 (18) | (T) |
| PBAb | 1.572 (2) | (L) | 1.369 (2) | (S) | 1.354 (2) | (S) |
| PBPBAc | 1.526 (2) | (S) | 1.358 (2) | (S) | 1.358 (2) | (S) |
| MPBAd | 1.576 (2) | (L) | 1.362 (2) | (S) | 1.352 (2) | (S) |
| DFPHBe | 1.576 (2) | (L) | 1.351 (2) | (S) | 1.341 (2) | (S) |
| FPBAf | 1.572 (2) | (L) | 1.371 (2) | (E) | 1.363 (2) | (E) |
| APBAMg | 1.580 (2) | (L) | 1.363 (2) | (S) | 1.362 (2) | (S) |
| DBPACh | 1.564 (2) | (L) | 1.369 (2) | (S) | 1.364 (2) | (E) |
| BPAi | 1.581 (2) | (L) | 1.376 (2) | (L) | 1.345 (2) | (S) |
| PNNRPBAj | 1.567 (2) | (L) | 1.357 (2) | (S) | 1.353 (2) | (S) |
| HDPBBDMk | 1.582 (2) | (L) | 1.375 (2) | (L) | 1.323 (2) | (S) |
| AFPBAl | 1.554 (2) | (S) | 1.371 (2) | (E) | 1.367 (2) | (L) |
| BTFMPDBm | 1.597 (2) | (L) | 1.360 (2) | (S) | 1.355 (2) | (S) |
| PABTFMPn | 1.561 (2) | (L) | 1.365 (2) | (S) | 1.343 (2) | (S) |
| CTBPFPBo | 1.615 (2) | (L) | 1.535 (2) | (L) | 1.520 (2) | (L) |
| CTBPFPBo | 1.612 (2) | (L) | 1.526 (2) | (L) | 1.519 (2) | (L) |
| CTBPFPBo | 1.611 (2) | (L) | 1.529 (2) | (L) | 1.525 (2) | (L) |
| PFBBAp | 1.566 (2) | (L) | 1.366 (2) | (S) | 1.357 (2) | (S) |
| FBBAq | 1.585 (2) | (L) | 1.358 (2) | (S) | 1.351 (2) | (S) |
| EDBAr | 1.573 (2) | (L) | 1.371 (2) | (E) | 1.364 (2) | (E) |
| CNBBAs | 1.587 (2) | (L) | 1.365 (2) | (S) | 1.345 (2) | (S) |
| MIMBBAt | 1.596 (2) | (L) | 1.346 (2) | (S) | 1.342 (2) | (S) |
| Notes: (a) This work;
(b) Rettig & Trotter (1997) [PBA is phenylboronic acid];
(c) Zvonkova, & Gluskova (1958) [PBPBA is p-Bromophenylboronic acid];
(d) Zheng et al. (2001) [MPBA is 4-Methylphenylboronic acid];
(e) Bradley et al. (1996) [DFPHB is (2,6-Difluorophenyl)dihydroxyborane];
(f) Fronczek et al. (2001) [FPBA is 4-Formylphenylboronic acid];
(g) Ganguly et al. (2003) [FPBA is 2-Acetylphenylboronic acid monohydrate];
(h) Li, et al. (1995) [DBPAC is 3-(Dihydroxyboryl)phenylammonium chloride];
(i) Shull et al. (2000) [BPA is L-p-Boronophenylalanine];
(j) Akita et al. (1995) [PNNRPBA is Phenyl nitronyl nitroxide radical
phenylboronic acid];
(k) Dreos et al. (2003) [HDPBBDM is (O,O'-(Hydroxy
(4-(dihydroxyboryl) phenyl)boron)
-bis(dimethylglyoximato))-aqua-methyl-cobalt trihydrate];
(l) Das et al. (2003) [AFPBA is 4-Amino-3-fluorophenylboronic acid];
(m) Cornet et al. (2003) [BTFMPDB is 6-bis(Trifluoromethyl)
phenyl)-dihydroxy-borane];
(n) Reetz et al. (1994) [PABTFMP is Phenylalanine 3,5-bis(trifluoromethyl)
phenylbonic acid 18-crown-6];
(o) Beringhelli et al. (2003) [CTBPFPB is Cyclo-tris(bis(pentafluorophenyl)
borinic acid)];
(p) Feulner et al. (1990) [PFBBA is p-Formylbenzeneboronic acid];
(q) Scouten et al. (1994) [FBBA is o-Formylbenzeneboronic acid];
(r) Pilkington et al. (1995) [EDBA is 2,2'-Ethynylenedibenzeneboronic acid];
(s) Soundararajan et al. (1993) [CNBBA is 4-Carboxy-2-nitrobenzeneboronic
acid];
(t) Scouten et al. (1994) [MIMBBA is o-Methoxyiminomethylbenzeneboronic acid]. |
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