Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055389/kj2069sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055389/kj2069Isup2.hkl |
CCDC reference: 672882
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.108
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.47 From the CIF: _reflns_number_total 1657 Count of symmetry unique reflns 1662 Completeness (_total/calc) 99.70% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Zhang et al. (2007); Chen et al. (2006); Deutsch & Osoling (1949).
The synthesis of (I) was described previously (Zhang et al., 2007). Single crystals suitable for X-ray analysis were obtained by slow evaporation of a water solution at room temperature.
Friedel pairs were merged prior to refinement using SHELXTL (Bruker, 2000). The positions of the H atoms were determined using the difference map and were refined isotropically. The H atoms on O2 and O3 were disordered over 2 sites with 50% occupancy in each site. The disordered H atoms were refined with one common Uiso.
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C9H10BNO3 | F(000) = 1600 |
Mr = 190.99 | Dx = 1.280 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 2853 reflections |
a = 18.626 (4) Å | θ = 2.4–25.1° |
b = 42.112 (8) Å | µ = 0.09 mm−1 |
c = 5.0536 (10) Å | T = 295 K |
V = 3963.9 (13) Å3 | Needle, colourless |
Z = 16 | 0.43 × 0.18 × 0.12 mm |
Bruker APEXII CCD diffractometer | 1657 independent reflections |
Radiation source: fine-focus sealed tube | 1279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 30.5°, θmin = 1.9° |
Absorption correction: numerical (face correction with APEX2; Bruker, 2006) | h = −26→25 |
Tmin = 0.87, Tmax = 0.99 | k = −59→59 |
14806 measured reflections | l = −7→2 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0606P)2 + 0.5557P] where P = (Fo2 + 2Fc2)/3 |
1657 reflections | (Δ/σ)max = 0.007 |
172 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.12 e Å−3 |
C9H10BNO3 | V = 3963.9 (13) Å3 |
Mr = 190.99 | Z = 16 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 18.626 (4) Å | µ = 0.09 mm−1 |
b = 42.112 (8) Å | T = 295 K |
c = 5.0536 (10) Å | 0.43 × 0.18 × 0.12 mm |
Bruker APEXII CCD diffractometer | 1657 independent reflections |
Absorption correction: numerical (face correction with APEX2; Bruker, 2006) | 1279 reflections with I > 2σ(I) |
Tmin = 0.87, Tmax = 0.99 | Rint = 0.035 |
14806 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 1 restraint |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.17 e Å−3 |
1657 reflections | Δρmin = −0.12 e Å−3 |
172 parameters |
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 | Occ. (<1) | |
O1 | 0.34232 (7) | 0.11569 (4) | 1.1454 (4) | 0.0653 (5) | |
O2 | 0.43076 (12) | 0.01158 (6) | 0.3738 (4) | 0.0779 (6) | |
H2A | 0.466 (3) | 0.0024 (17) | 0.394 (16) | 0.082 (10)* | 0.50 |
H2B | 0.413 (4) | 0.0131 (15) | 0.237 (17) | 0.082 (10)* | 0.50 |
O3 | 0.43531 (9) | 0.01566 (4) | 0.8312 (3) | 0.0569 (4) | |
H3A | 0.414 (4) | 0.0220 (15) | 0.944 (17) | 0.082 (10)* | 0.50 |
H3B | 0.478 (3) | 0.0072 (14) | 0.827 (14) | 0.082 (10)* | 0.50 |
N1 | 0.23312 (9) | 0.10547 (4) | 0.9628 (3) | 0.0476 (4) | |
H1A | 0.1859 (16) | 0.1131 (6) | 0.949 (6) | 0.072 (8)* | |
B1 | 0.39944 (13) | 0.02160 (6) | 0.6027 (5) | 0.0469 (5) | |
C1 | 0.24915 (10) | 0.08023 (4) | 0.7901 (4) | 0.0442 (4) | |
C2 | 0.19502 (12) | 0.07111 (5) | 0.6107 (5) | 0.0567 (5) | |
H2 | 0.1493 (13) | 0.0830 (5) | 0.624 (6) | 0.059 (6)* | |
C3 | 0.20685 (14) | 0.04743 (6) | 0.4318 (5) | 0.0633 (6) | |
H3 | 0.1704 (15) | 0.0419 (6) | 0.324 (7) | 0.068 (7)* | |
C4 | 0.27236 (13) | 0.03202 (5) | 0.4223 (4) | 0.0543 (5) | |
H4 | 0.2783 (13) | 0.0162 (6) | 0.288 (6) | 0.060 (7)* | |
C5 | 0.32638 (10) | 0.03966 (4) | 0.6037 (4) | 0.0447 (4) | |
C6 | 0.31372 (10) | 0.06372 (5) | 0.7880 (4) | 0.0433 (4) | |
H6 | 0.3479 (12) | 0.0696 (5) | 0.914 (5) | 0.055 (6)* | |
C7 | 0.27804 (10) | 0.12142 (5) | 1.1262 (4) | 0.0478 (4) | |
C8 | 0.24262 (14) | 0.14649 (6) | 1.2856 (6) | 0.0646 (6) | |
H8 | 0.1923 (18) | 0.1488 (7) | 1.258 (8) | 0.085 (9)* | |
C9 | 0.2770 (2) | 0.16236 (8) | 1.4653 (8) | 0.0938 (11) | |
H9A | 0.2548 (17) | 0.1772 (8) | 1.613 (9) | 0.101 (10)* | |
H9B | 0.322 (2) | 0.1570 (8) | 1.511 (9) | 0.105 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0357 (7) | 0.0729 (9) | 0.0873 (12) | 0.0017 (6) | −0.0151 (8) | −0.0233 (9) |
O2 | 0.0824 (15) | 0.1155 (17) | 0.0359 (9) | 0.0226 (11) | 0.0051 (9) | −0.0134 (10) |
O3 | 0.0593 (10) | 0.0778 (11) | 0.0334 (7) | 0.0152 (8) | −0.0019 (6) | −0.0005 (7) |
N1 | 0.0334 (8) | 0.0568 (9) | 0.0526 (9) | 0.0036 (7) | −0.0099 (7) | −0.0050 (8) |
B1 | 0.0551 (12) | 0.0549 (11) | 0.0307 (8) | 0.0020 (9) | 0.0008 (8) | −0.0002 (9) |
C1 | 0.0394 (9) | 0.0505 (10) | 0.0427 (9) | −0.0035 (8) | −0.0090 (7) | 0.0036 (8) |
C2 | 0.0463 (11) | 0.0635 (12) | 0.0602 (13) | −0.0005 (10) | −0.0215 (10) | −0.0013 (11) |
C3 | 0.0607 (13) | 0.0686 (14) | 0.0606 (13) | −0.0068 (11) | −0.0281 (11) | −0.0065 (11) |
C4 | 0.0648 (13) | 0.0559 (11) | 0.0421 (10) | −0.0038 (10) | −0.0128 (9) | −0.0034 (9) |
C5 | 0.0507 (10) | 0.0511 (10) | 0.0324 (8) | −0.0022 (8) | −0.0017 (7) | 0.0052 (8) |
C6 | 0.0380 (9) | 0.0550 (11) | 0.0370 (9) | −0.0014 (8) | −0.0066 (7) | −0.0001 (7) |
C7 | 0.0381 (9) | 0.0530 (10) | 0.0522 (10) | −0.0016 (8) | −0.0076 (8) | −0.0007 (9) |
C8 | 0.0525 (13) | 0.0653 (13) | 0.0760 (17) | 0.0114 (11) | −0.0125 (12) | −0.0159 (12) |
C9 | 0.081 (2) | 0.097 (2) | 0.104 (3) | 0.0237 (17) | −0.0317 (18) | −0.049 (2) |
O1—C7 | 1.225 (2) | C2—C3 | 1.364 (4) |
O2—B1 | 1.363 (3) | C2—H2 | 0.99 (2) |
O2—H2A | 0.76 (7) | C3—C4 | 1.383 (4) |
O2—H2B | 0.77 (8) | C3—H3 | 0.90 (3) |
O3—B1 | 1.357 (3) | C4—C5 | 1.399 (3) |
O3—H3A | 0.74 (8) | C4—H4 | 0.96 (3) |
O3—H3B | 0.87 (5) | C5—C6 | 1.396 (3) |
N1—C7 | 1.354 (3) | C6—H6 | 0.93 (3) |
N1—C1 | 1.407 (3) | C7—C8 | 1.483 (3) |
N1—H1A | 0.94 (3) | C8—C9 | 1.297 (4) |
B1—C5 | 1.559 (3) | C8—H8 | 0.95 (3) |
C1—C6 | 1.389 (3) | C9—H9A | 1.06 (4) |
C1—C2 | 1.409 (3) | C9—H9B | 0.89 (4) |
B1—O2—H2A | 114 (6) | C4—C3—H3 | 121.6 (17) |
B1—O2—H2B | 123 (6) | C3—C4—C5 | 120.3 (2) |
H2A—O2—H2B | 122 (8) | C3—C4—H4 | 116.9 (15) |
B1—O3—H3A | 109 (6) | C5—C4—H4 | 122.9 (15) |
B1—O3—H3B | 120 (5) | C6—C5—C4 | 118.86 (18) |
H3A—O3—H3B | 131 (7) | C6—C5—B1 | 120.24 (17) |
C7—N1—C1 | 128.46 (17) | C4—C5—B1 | 120.90 (19) |
C7—N1—H1A | 117.1 (18) | C1—C6—C5 | 120.95 (16) |
C1—N1—H1A | 114.2 (18) | C1—C6—H6 | 117.0 (14) |
O3—B1—O2 | 117.0 (2) | C5—C6—H6 | 122.0 (14) |
O3—B1—C5 | 121.1 (2) | O1—C7—N1 | 123.7 (2) |
O2—B1—C5 | 121.8 (2) | O1—C7—C8 | 122.2 (2) |
C6—C1—N1 | 124.49 (16) | N1—C7—C8 | 114.19 (18) |
C6—C1—C2 | 118.57 (19) | C9—C8—C7 | 121.8 (3) |
N1—C1—C2 | 116.93 (18) | C9—C8—H8 | 122 (2) |
C3—C2—C1 | 120.7 (2) | C7—C8—H8 | 116 (2) |
C3—C2—H2 | 123.6 (16) | C8—C9—H9A | 127.2 (19) |
C1—C2—H2 | 115.7 (15) | C8—C9—H9B | 121 (2) |
C2—C3—C4 | 120.6 (2) | H9A—C9—H9B | 109 (3) |
C2—C3—H3 | 117.8 (18) | ||
C7—N1—C1—C6 | 10.7 (3) | O3—B1—C5—C4 | −145.3 (2) |
C7—N1—C1—C2 | −170.2 (2) | O2—B1—C5—C4 | 35.9 (3) |
C6—C1—C2—C3 | −2.6 (3) | N1—C1—C6—C5 | −177.70 (18) |
N1—C1—C2—C3 | 178.2 (2) | C2—C1—C6—C5 | 3.2 (3) |
C1—C2—C3—C4 | −0.3 (4) | C4—C5—C6—C1 | −0.9 (3) |
C2—C3—C4—C5 | 2.6 (4) | B1—C5—C6—C1 | 179.45 (19) |
C3—C4—C5—C6 | −2.0 (3) | C1—N1—C7—O1 | 0.3 (3) |
C3—C4—C5—B1 | 177.6 (2) | C1—N1—C7—C8 | −178.9 (2) |
O3—B1—C5—C6 | 34.3 (3) | O1—C7—C8—C9 | −4.2 (4) |
O2—B1—C5—C6 | −144.5 (2) | N1—C7—C8—C9 | 174.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O2i | 0.77 (7) | 2.02 (7) | 2.759 (3) | 163 (7) |
O2—H2B···O3ii | 0.77 (8) | 2.10 (9) | 2.748 (3) | 143 (7) |
O3—H3A···O2iii | 0.75 (8) | 2.24 (8) | 2.748 (3) | 126 (7) |
O3—H3B···O3i | 0.87 (5) | 1.88 (5) | 2.746 (3) | 173 (6) |
N1—H1A···O1iv | 0.93 (3) | 1.98 (3) | 2.911 (3) | 172 (2) |
Symmetry codes: (i) −x+1, −y, z; (ii) x, y, z−1; (iii) x, y, z+1; (iv) x−1/4, −y+1/4, z−1/4. |
Experimental details
Crystal data | |
Chemical formula | C9H10BNO3 |
Mr | 190.99 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 295 |
a, b, c (Å) | 18.626 (4), 42.112 (8), 5.0536 (10) |
V (Å3) | 3963.9 (13) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.43 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Numerical (face correction with APEX2; Bruker, 2006) |
Tmin, Tmax | 0.87, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14806, 1657, 1279 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.713 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.108, 1.04 |
No. of reflections | 1657 |
No. of parameters | 172 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.12 |
Computer programs: APEX2 (Bruker, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O2i | 0.77 (7) | 2.02 (7) | 2.759 (3) | 163 (7) |
O2—H2B···O3ii | 0.77 (8) | 2.10 (9) | 2.748 (3) | 143 (7) |
O3—H3A···O2iii | 0.75 (8) | 2.24 (8) | 2.748 (3) | 126 (7) |
O3—H3B···O3i | 0.87 (5) | 1.88 (5) | 2.746 (3) | 173 (6) |
N1—H1A···O1iv | 0.93 (3) | 1.98 (3) | 2.911 (3) | 172 (2) |
Symmetry codes: (i) −x+1, −y, z; (ii) x, y, z−1; (iii) x, y, z+1; (iv) x−1/4, −y+1/4, z−1/4. |
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The title compound is a monomer containing a boronate group, which can form complexes with cis diols at pH values above 9 (Deutsch & Osoling, 1949). This interaction can be employed for affinity chromatography and glucose sensing (Chen et al., 2006).
The molecular structure of the title compound is illustrated in Fig.1. Weak N—H···O and O—H···O hydrogen bonding interactions are observed in the molecular structure which help to stabilize the crystal structure and forming an infinite threedimensional network, as illustrated in the packing diagram displayed in Fig. 2. The dihedral angle between the benzene ring and the plane composed of O2—B1—O3 is 35.12(0.23)°.