Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014480/lh6421sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014480/lh6421Isup2.hkl |
CCDC reference: 274581
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.070
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT411_ALERT_2_C Short Inter H...H Contact H2 .. H16 .. 2.14 Ang.
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 28.20 From the CIF: _reflns_number_total 2400 Count of symmetry unique reflns 2414 Completeness (_total/calc) 99.42% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor 1997); 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: WinGX (Farrugia, 1999).
C18H18B2O6 | F(000) = 736 |
Mr = 351.94 | Dx = 1.356 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 24578 reflections |
a = 10.2706 (1) Å | θ = 3.6–28.2° |
b = 12.5577 (2) Å | µ = 0.10 mm−1 |
c = 13.3708 (2) Å | T = 123 K |
V = 1724.50 (4) Å3 | Prismatic, colourless |
Z = 4 | 0.31 × 0.27 × 0.24 mm |
Nonius KappaCCD area-detector diffractometer | Rint = 0.039 |
CCD rotation images, thick slices scans | θmax = 28.2°, θmin = 3.6° |
24578 measured reflections | h = −12→13 |
2400 independent reflections | k = −16→16 |
2188 reflections with I > 2σ(I) | l = −17→17 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0297P)2 + 0.427P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.07 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.20 e Å−3 |
2400 reflections | Δρmin = −0.19 e Å−3 |
236 parameters |
Experimental. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz, δ, p.p.m.): 7.83–7.89 (4H, m, m-ArH), 7.35–7.56 (6H, m, o,p-ArH), 6.22 (1H, d, J = 4 Hz, H1), 5.03 (1H, d, J = 4 Hz, H2), 4.74 (1H, d, J = 2 Hz, H3), 4.50 (1H, t, J = 4 Hz, H5), 4.32 (1H, d, J = 3 Hz, H4), 3.90 (1H, br. d, J = 12 Hz, H6'), 3.74 (1H, br d, J = 12 Hz, H6), 1.90 (1H, br s, –OH). 13C NMR (CDCl3, 100 MHz, δ, p.p.m.): 64.1, 70.8, 74.2, 75.0, 86.4, 104.5, 127.7, 128.0, 131.2, 132.3, 134.0, 135.2. mp 155–158°C [literature value (Wood & Siddiqui, 1974) 159–162°C] |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 8.4160 (0.0043) x - 1.3672 (0.0098) y + 7.5244 (0.0078) z = 1.4501 (0.0039) * -0.0005 (0.0005) O2 * -0.0004 (0.0005) O3 * 0.0013 (0.0015) B1 * -0.0004 (0.0004) C7 Rms deviation of fitted atoms = 0.0007 0.3385 (0.0079) x - 2.4783 (0.0100) y - 13.1004 (0.0022) z = 2.0478 (0.0009) Angle to previous plane (with approximate e.s.d.) = 59.81 (0.06) * -0.0057 (0.0005) O4 * -0.0057 (0.0005) O5 * 0.0169 (0.0016) B2 * -0.0055 (0.0005) C13 Rms deviation of fitted atoms = 0.0098 |
x | y | z | Uiso*/Ueq | ||
C1 | 0.14693 (15) | 0.14507 (12) | −0.01045 (12) | 0.0166 (3) | |
H1 | 0.1248 | 0.0804 | 0.0297 | 0.02* | |
C2 | 0.26059 (15) | 0.12096 (12) | −0.07984 (12) | 0.0167 (3) | |
H2 | 0.3282 | 0.0763 | −0.046 | 0.02* | |
C3 | 0.19578 (16) | 0.06149 (13) | −0.16529 (13) | 0.0180 (3) | |
H3 | 0.2409 | 0.0735 | −0.2306 | 0.022* | |
C4 | 0.05455 (16) | 0.10426 (13) | −0.16576 (13) | 0.0200 (3) | |
H4 | 0.0359 | 0.1455 | −0.2281 | 0.024* | |
C5 | 0.16591 (16) | 0.23996 (13) | 0.05853 (12) | 0.0180 (3) | |
H5 | 0.078 | 0.2621 | 0.0831 | 0.022* | |
C6 | 0.24867 (17) | 0.21358 (14) | 0.14948 (13) | 0.0223 (4) | |
H6A | 0.2679 | 0.2802 | 0.1863 | 0.027* | |
H6B | 0.1983 | 0.1666 | 0.1946 | 0.027* | |
C7 | 0.35669 (15) | 0.41226 (12) | −0.13139 (12) | 0.0169 (3) | |
C8 | 0.36261 (16) | 0.51173 (13) | −0.08414 (13) | 0.0208 (3) | |
H8 | 0.3263 | 0.5201 | −0.0193 | 0.025* | |
C9 | 0.42094 (17) | 0.59859 (14) | −0.13096 (14) | 0.0241 (4) | |
H9 | 0.4252 | 0.6653 | −0.0976 | 0.029* | |
C10 | 0.47257 (18) | 0.58772 (14) | −0.22585 (15) | 0.0259 (4) | |
H10 | 0.5115 | 0.6472 | −0.258 | 0.031* | |
C11 | 0.46770 (18) | 0.48998 (15) | −0.27432 (14) | 0.0267 (4) | |
H11 | 0.5031 | 0.4826 | −0.3396 | 0.032* | |
C12 | 0.41083 (16) | 0.40307 (14) | −0.22705 (13) | 0.0220 (4) | |
H12 | 0.4087 | 0.3362 | −0.2603 | 0.026* | |
C13 | −0.00195 (17) | −0.18707 (14) | −0.12055 (13) | 0.0205 (3) | |
C14 | 0.07931 (19) | −0.27313 (14) | −0.09803 (13) | 0.0247 (4) | |
H14 | 0.171 | −0.2635 | −0.0972 | 0.03* | |
C15 | 0.0270 (2) | −0.37260 (16) | −0.07681 (15) | 0.0345 (5) | |
H15 | 0.0829 | −0.4307 | −0.0616 | 0.041* | |
C16 | −0.1069 (2) | −0.38711 (17) | −0.07788 (15) | 0.0361 (5) | |
H16 | −0.1424 | −0.4553 | −0.0639 | 0.043* | |
C17 | −0.1889 (2) | −0.30277 (17) | −0.09925 (14) | 0.0310 (4) | |
H17 | −0.2806 | −0.3128 | −0.0989 | 0.037* | |
C18 | −0.13688 (18) | −0.20344 (15) | −0.12116 (14) | 0.0253 (4) | |
H18 | −0.1934 | −0.1459 | −0.1367 | 0.03* | |
B1 | 0.29360 (17) | 0.31387 (15) | −0.07848 (15) | 0.0173 (4) | |
B2 | 0.05300 (19) | −0.07408 (15) | −0.14222 (14) | 0.0197 (4) | |
O1 | 0.04146 (11) | 0.16916 (9) | −0.07939 (9) | 0.0192 (3) | |
O2 | 0.22096 (11) | 0.32876 (9) | 0.00524 (9) | 0.0191 (3) | |
O3 | 0.31547 (11) | 0.21631 (9) | −0.12089 (9) | 0.0187 (3) | |
O4 | −0.02558 (12) | 0.01235 (9) | −0.15888 (9) | 0.0225 (3) | |
O5 | 0.18344 (11) | −0.04988 (9) | −0.14170 (9) | 0.0196 (3) | |
O6 | 0.36827 (12) | 0.16243 (9) | 0.12446 (10) | 0.0237 (3) | |
H6 | 0.4213 | 0.2079 | 0.1029 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0139 (8) | 0.0158 (7) | 0.0201 (8) | −0.0002 (6) | −0.0002 (6) | 0.0026 (6) |
C2 | 0.0161 (7) | 0.0128 (7) | 0.0213 (8) | −0.0011 (6) | 0.0015 (7) | 0.0023 (6) |
C3 | 0.0196 (8) | 0.0147 (7) | 0.0197 (8) | 0.0000 (6) | 0.0011 (7) | 0.0017 (6) |
C4 | 0.0219 (8) | 0.0182 (8) | 0.0198 (8) | 0.0003 (7) | −0.0016 (7) | 0.0001 (7) |
C5 | 0.0178 (8) | 0.0170 (8) | 0.0191 (8) | −0.0025 (6) | 0.0043 (7) | 0.0010 (7) |
C6 | 0.0220 (9) | 0.0260 (9) | 0.0189 (8) | −0.0042 (7) | 0.0017 (7) | 0.0006 (7) |
C7 | 0.0148 (7) | 0.0161 (7) | 0.0197 (8) | −0.0002 (6) | −0.0024 (6) | 0.0033 (6) |
C8 | 0.0207 (8) | 0.0206 (8) | 0.0209 (8) | −0.0010 (7) | 0.0003 (7) | 0.0015 (7) |
C9 | 0.0252 (9) | 0.0165 (8) | 0.0305 (9) | −0.0022 (7) | −0.0033 (8) | 0.0011 (7) |
C10 | 0.0255 (9) | 0.0220 (8) | 0.0301 (9) | −0.0056 (7) | −0.0007 (8) | 0.0107 (7) |
C11 | 0.0295 (10) | 0.0294 (9) | 0.0213 (9) | −0.0047 (8) | 0.0055 (7) | 0.0060 (8) |
C12 | 0.0222 (9) | 0.0199 (8) | 0.0240 (8) | −0.0016 (7) | 0.0001 (7) | −0.0001 (7) |
C13 | 0.0232 (9) | 0.0204 (8) | 0.0178 (8) | −0.0034 (7) | −0.0004 (7) | −0.0039 (7) |
C14 | 0.0291 (9) | 0.0237 (9) | 0.0212 (8) | −0.0023 (7) | −0.0053 (8) | 0.0002 (7) |
C15 | 0.0486 (12) | 0.0253 (10) | 0.0297 (10) | −0.0036 (9) | −0.0094 (9) | 0.0089 (8) |
C16 | 0.0532 (13) | 0.0312 (11) | 0.0240 (9) | −0.0192 (10) | 0.0002 (9) | 0.0066 (9) |
C17 | 0.0311 (10) | 0.0386 (11) | 0.0234 (9) | −0.0157 (9) | 0.0049 (8) | −0.0069 (8) |
C18 | 0.0255 (9) | 0.0262 (9) | 0.0243 (9) | −0.0031 (7) | 0.0014 (8) | −0.0081 (8) |
B1 | 0.0145 (8) | 0.0167 (9) | 0.0207 (9) | 0.0002 (7) | −0.0005 (7) | 0.0041 (7) |
B2 | 0.0198 (9) | 0.0214 (9) | 0.0178 (9) | −0.0003 (7) | −0.0029 (8) | −0.0043 (7) |
O1 | 0.0169 (6) | 0.0192 (6) | 0.0215 (6) | 0.0028 (5) | −0.0022 (5) | −0.0023 (5) |
O2 | 0.0209 (6) | 0.0148 (5) | 0.0216 (6) | −0.0022 (5) | 0.0038 (5) | 0.0007 (5) |
O3 | 0.0196 (6) | 0.0140 (5) | 0.0224 (6) | −0.0023 (4) | 0.0054 (5) | 0.0018 (5) |
O4 | 0.0191 (6) | 0.0196 (6) | 0.0287 (7) | −0.0014 (5) | −0.0039 (5) | −0.0020 (5) |
O5 | 0.0196 (6) | 0.0133 (5) | 0.0258 (6) | −0.0006 (4) | −0.0008 (5) | −0.0005 (5) |
O6 | 0.0211 (6) | 0.0203 (6) | 0.0298 (7) | −0.0027 (5) | −0.0022 (6) | 0.0020 (5) |
C1—O1 | 1.4542 (19) | C9—C10 | 1.382 (3) |
C1—C5 | 1.519 (2) | C9—H9 | 0.95 |
C1—C2 | 1.522 (2) | C10—C11 | 1.389 (3) |
C1—H1 | 1 | C10—H10 | 0.95 |
C2—O3 | 1.4327 (18) | C11—C12 | 1.390 (2) |
C2—C3 | 1.519 (2) | C11—H11 | 0.95 |
C2—H2 | 1 | C12—H12 | 0.95 |
C3—O5 | 1.4392 (19) | C13—C14 | 1.398 (2) |
C3—C4 | 1.547 (2) | C13—C18 | 1.401 (2) |
C3—H3 | 1 | C13—B2 | 1.554 (2) |
C4—O1 | 1.420 (2) | C14—C15 | 1.389 (3) |
C4—O4 | 1.420 (2) | C14—H14 | 0.95 |
C4—H4 | 1 | C15—C16 | 1.387 (3) |
C5—O2 | 1.4390 (19) | C15—H15 | 0.95 |
C5—C6 | 1.520 (2) | C16—C17 | 1.383 (3) |
C5—H5 | 1 | C16—H16 | 0.95 |
C6—O6 | 1.426 (2) | C17—C18 | 1.388 (3) |
C6—H6A | 0.99 | C17—H17 | 0.95 |
C6—H6B | 0.99 | C18—H18 | 0.95 |
C7—C12 | 1.399 (2) | B1—O2 | 1.358 (2) |
C7—C8 | 1.401 (2) | B1—O3 | 1.369 (2) |
C7—B1 | 1.564 (2) | B2—O4 | 1.371 (2) |
C8—C9 | 1.393 (2) | B2—O5 | 1.374 (2) |
C8—H8 | 0.95 | O6—H6 | 0.84 |
O1—C1—C5 | 108.50 (12) | C10—C9—C8 | 120.02 (17) |
O1—C1—C2 | 103.08 (13) | C10—C9—H9 | 120 |
C5—C1—C2 | 115.33 (13) | C8—C9—H9 | 120 |
O1—C1—H1 | 109.9 | C9—C10—C11 | 120.13 (16) |
C5—C1—H1 | 109.9 | C9—C10—H10 | 119.9 |
C2—C1—H1 | 109.9 | C11—C10—H10 | 119.9 |
O3—C2—C3 | 107.17 (13) | C10—C11—C12 | 119.79 (16) |
O3—C2—C1 | 111.66 (12) | C10—C11—H11 | 120.1 |
C3—C2—C1 | 102.73 (13) | C12—C11—H11 | 120.1 |
O3—C2—H2 | 111.6 | C11—C12—C7 | 121.19 (16) |
C3—C2—H2 | 111.6 | C11—C12—H12 | 119.4 |
C1—C2—H2 | 111.6 | C7—C12—H12 | 119.4 |
O5—C3—C2 | 110.59 (13) | C14—C13—C18 | 118.57 (17) |
O5—C3—C4 | 104.82 (12) | C14—C13—B2 | 121.94 (15) |
C2—C3—C4 | 104.08 (13) | C18—C13—B2 | 119.48 (16) |
O5—C3—H3 | 112.3 | C15—C14—C13 | 120.53 (18) |
C2—C3—H3 | 112.3 | C15—C14—H14 | 119.7 |
C4—C3—H3 | 112.3 | C13—C14—H14 | 119.7 |
O1—C4—O4 | 111.03 (13) | C16—C15—C14 | 120.0 (2) |
O1—C4—C3 | 106.55 (13) | C16—C15—H15 | 120 |
O4—C4—C3 | 105.13 (13) | C14—C15—H15 | 120 |
O1—C4—H4 | 111.3 | C17—C16—C15 | 120.36 (19) |
O4—C4—H4 | 111.3 | C17—C16—H16 | 119.8 |
C3—C4—H4 | 111.3 | C15—C16—H16 | 119.8 |
O2—C5—C1 | 110.95 (13) | C16—C17—C18 | 119.81 (18) |
O2—C5—C6 | 110.20 (13) | C16—C17—H17 | 120.1 |
C1—C5—C6 | 112.73 (14) | C18—C17—H17 | 120.1 |
O2—C5—H5 | 107.6 | C17—C18—C13 | 120.75 (19) |
C1—C5—H5 | 107.6 | C17—C18—H18 | 119.6 |
C6—C5—H5 | 107.6 | C13—C18—H18 | 119.6 |
O6—C6—C5 | 113.08 (14) | O2—B1—O3 | 123.70 (15) |
O6—C6—H6A | 109 | O2—B1—C7 | 119.44 (15) |
C5—C6—H6A | 109 | O3—B1—C7 | 116.86 (15) |
O6—C6—H6B | 109 | O4—B2—O5 | 113.57 (15) |
C5—C6—H6B | 109 | O4—B2—C13 | 122.64 (15) |
H6A—C6—H6B | 107.8 | O5—B2—C13 | 123.72 (16) |
C12—C7—C8 | 117.93 (15) | C4—O1—C1 | 109.01 (12) |
C12—C7—B1 | 120.85 (15) | B1—O2—C5 | 121.15 (13) |
C8—C7—B1 | 121.22 (15) | B1—O3—C2 | 121.66 (13) |
C9—C8—C7 | 120.94 (16) | B2—O4—C4 | 108.22 (13) |
C9—C8—H8 | 119.5 | B2—O5—C3 | 107.44 (13) |
C7—C8—H8 | 119.5 | C6—O6—H6 | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O1i | 0.84 | 2.00 | 2.8283 (17) | 168 |
Symmetry code: (i) x+1/2, −y+1/2, −z. |