addenda and errata
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one. Corrigendum
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my, suchada.c@psu.ac.th
In the paper by Teh, Fun, Razak, Chantrapromma, Boonnak & Karalai [Acta Cryst. (2005), E61, o3715–o3717], the data collection temperature is given incorrectly. The correct temperature is given below and in the revised `Key indicators'.
2. Crystal data
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Supporting information
Data collection: APEX2 (Bruker, 2005); cell
APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).C17H14O5 | F(000) = 624 |
Mr = 298.28 | Dx = 1.449 Mg m−3 |
Monoclinic, P21/c | Melting point = 447–448 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.9406 (4) Å | Cell parameters from 3581 reflections |
b = 3.8619 (1) Å | θ = 2.0–28.0° |
c = 21.7968 (4) Å | µ = 0.11 mm−1 |
β = 106.52 (1)° | T = 297 K |
V = 1367.15 (9) Å3 | Plate, colourless |
Z = 4 | 0.54 × 0.15 × 0.08 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 3283 independent reflections |
Radiation source: fine-focus sealed tube | 2207 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.0°, θmin = 2.0° |
ω scans | h = −21→22 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −5→5 |
Tmin = 0.912, Tmax = 0.992 | l = −28→28 |
17884 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.2601P] where P = (Fo2 + 2Fc2)/3 |
3283 reflections | (Δ/σ)max = 0.001 |
201 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.21 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 | ||
O1 | 0.15499 (6) | 0.9753 (3) | 0.37516 (4) | 0.0409 (3) | |
O2 | 0.25586 (7) | 0.5256 (3) | 0.54929 (5) | 0.0541 (4) | |
O3 | 0.39800 (7) | 0.5554 (4) | 0.52901 (5) | 0.0560 (4) | |
H3 | 0.3636 | 0.5130 | 0.5479 | 0.084* | |
O4 | 0.40678 (7) | 1.0285 (3) | 0.32828 (5) | 0.0538 (4) | |
O5 | −0.22834 (7) | 1.0817 (4) | 0.28553 (5) | 0.0533 (4) | |
C1 | 0.23874 (9) | 0.9148 (4) | 0.39514 (7) | 0.0362 (4) | |
C2 | 0.28282 (10) | 1.0058 (4) | 0.35373 (7) | 0.0412 (4) | |
H2 | 0.2573 | 1.1094 | 0.3146 | 0.049* | |
C3 | 0.36683 (10) | 0.9380 (5) | 0.37218 (7) | 0.0414 (4) | |
C4 | 0.40646 (10) | 0.7874 (5) | 0.43095 (7) | 0.0440 (4) | |
H4 | 0.4628 | 0.7452 | 0.4424 | 0.053* | |
C5 | 0.36052 (10) | 0.7022 (5) | 0.47179 (7) | 0.0412 (4) | |
C6 | 0.27504 (9) | 0.7617 (4) | 0.45482 (6) | 0.0362 (4) | |
C7 | 0.22512 (10) | 0.6656 (4) | 0.49571 (7) | 0.0397 (4) | |
C8 | 0.13922 (10) | 0.7345 (5) | 0.47088 (7) | 0.0411 (4) | |
H8 | 0.1045 | 0.6780 | 0.4956 | 0.049* | |
C9 | 0.10645 (9) | 0.8792 (4) | 0.41260 (6) | 0.0362 (4) | |
C10 | 0.01916 (10) | 0.9446 (4) | 0.38162 (6) | 0.0355 (4) | |
C11 | −0.04119 (10) | 0.8394 (5) | 0.40996 (7) | 0.0424 (4) | |
H11 | −0.0249 | 0.7380 | 0.4503 | 0.051* | |
C12 | −0.12400 (10) | 0.8807 (5) | 0.38018 (7) | 0.0424 (4) | |
H12 | −0.1628 | 0.8085 | 0.4002 | 0.051* | |
C13 | −0.14880 (10) | 1.0311 (4) | 0.31993 (7) | 0.0399 (4) | |
C14 | −0.08988 (10) | 1.1419 (5) | 0.29100 (7) | 0.0444 (4) | |
H14 | −0.1064 | 1.2448 | 0.2508 | 0.053* | |
C15 | −0.00750 (10) | 1.1007 (5) | 0.32127 (7) | 0.0411 (4) | |
H15 | 0.0311 | 1.1775 | 0.3014 | 0.049* | |
C16 | 0.49030 (11) | 0.9268 (6) | 0.33992 (9) | 0.0601 (5) | |
H16A | 0.5094 | 0.9900 | 0.3040 | 0.090* | |
H16B | 0.4947 | 0.6806 | 0.3460 | 0.090* | |
H16C | 0.5233 | 1.0410 | 0.3777 | 0.090* | |
C17 | −0.29207 (11) | 0.9581 (6) | 0.31075 (9) | 0.0553 (5) | |
H17A | −0.3447 | 1.0069 | 0.2810 | 0.083* | |
H17B | −0.2882 | 1.0716 | 0.3507 | 0.083* | |
H17C | −0.2862 | 0.7127 | 0.3175 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0397 (6) | 0.0506 (7) | 0.0330 (5) | 0.0022 (5) | 0.0113 (4) | 0.0064 (5) |
O2 | 0.0556 (7) | 0.0711 (9) | 0.0343 (5) | 0.0069 (7) | 0.0107 (5) | 0.0164 (6) |
O3 | 0.0481 (7) | 0.0774 (10) | 0.0384 (6) | 0.0072 (7) | 0.0054 (5) | 0.0148 (6) |
O4 | 0.0448 (7) | 0.0732 (10) | 0.0467 (6) | 0.0002 (7) | 0.0183 (5) | 0.0100 (6) |
O5 | 0.0428 (6) | 0.0721 (9) | 0.0436 (6) | 0.0051 (7) | 0.0102 (5) | 0.0118 (6) |
C1 | 0.0377 (8) | 0.0370 (9) | 0.0324 (7) | −0.0006 (7) | 0.0075 (6) | −0.0016 (6) |
C2 | 0.0455 (9) | 0.0460 (11) | 0.0310 (7) | −0.0009 (8) | 0.0093 (6) | 0.0042 (7) |
C3 | 0.0440 (9) | 0.0453 (11) | 0.0363 (7) | −0.0039 (8) | 0.0136 (6) | −0.0008 (7) |
C4 | 0.0385 (8) | 0.0506 (11) | 0.0408 (8) | −0.0007 (8) | 0.0079 (6) | −0.0003 (8) |
C5 | 0.0453 (9) | 0.0430 (10) | 0.0323 (7) | 0.0006 (8) | 0.0060 (6) | 0.0003 (7) |
C6 | 0.0425 (8) | 0.0351 (9) | 0.0295 (6) | 0.0002 (8) | 0.0078 (6) | −0.0008 (6) |
C7 | 0.0499 (9) | 0.0383 (10) | 0.0304 (7) | 0.0008 (8) | 0.0106 (6) | 0.0004 (7) |
C8 | 0.0458 (9) | 0.0459 (10) | 0.0337 (7) | 0.0021 (8) | 0.0150 (6) | 0.0028 (7) |
C9 | 0.0446 (9) | 0.0345 (9) | 0.0319 (7) | −0.0008 (8) | 0.0149 (6) | −0.0026 (6) |
C10 | 0.0432 (8) | 0.0323 (9) | 0.0320 (7) | 0.0016 (7) | 0.0125 (6) | −0.0007 (6) |
C11 | 0.0475 (9) | 0.0475 (11) | 0.0328 (7) | 0.0007 (9) | 0.0125 (6) | 0.0071 (7) |
C12 | 0.0459 (9) | 0.0463 (11) | 0.0379 (7) | −0.0017 (8) | 0.0165 (7) | 0.0036 (7) |
C13 | 0.0423 (9) | 0.0410 (10) | 0.0359 (7) | 0.0044 (8) | 0.0102 (6) | −0.0007 (7) |
C14 | 0.0504 (10) | 0.0499 (11) | 0.0341 (7) | 0.0062 (9) | 0.0140 (7) | 0.0075 (7) |
C15 | 0.0473 (9) | 0.0438 (10) | 0.0361 (7) | 0.0027 (8) | 0.0183 (7) | 0.0053 (7) |
C16 | 0.0520 (11) | 0.0720 (14) | 0.0629 (11) | 0.0021 (11) | 0.0269 (9) | 0.0062 (10) |
C17 | 0.0429 (9) | 0.0675 (14) | 0.0551 (10) | −0.0014 (10) | 0.0131 (8) | 0.0029 (10) |
O1—C9 | 1.3645 (17) | C8—C9 | 1.354 (2) |
O1—C1 | 1.3804 (18) | C8—H8 | 0.93 |
O2—C7 | 1.2578 (17) | C9—C10 | 1.462 (2) |
O3—C5 | 1.3526 (18) | C10—C11 | 1.397 (2) |
O3—H3 | 0.82 | C10—C15 | 1.400 (2) |
O4—C3 | 1.3652 (19) | C11—C12 | 1.377 (2) |
O4—C16 | 1.420 (2) | C11—H11 | 0.93 |
O5—C13 | 1.3570 (18) | C12—C13 | 1.387 (2) |
O5—C17 | 1.426 (2) | C12—H12 | 0.93 |
C1—C2 | 1.371 (2) | C13—C14 | 1.391 (2) |
C1—C6 | 1.402 (2) | C14—C15 | 1.373 (2) |
C2—C3 | 1.389 (2) | C14—H14 | 0.93 |
C2—H2 | 0.93 | C15—H15 | 0.93 |
C3—C4 | 1.393 (2) | C16—H16A | 0.96 |
C4—C5 | 1.379 (2) | C16—H16B | 0.96 |
C4—H4 | 0.93 | C16—H16C | 0.96 |
C5—C6 | 1.408 (2) | C17—H17A | 0.96 |
C6—C7 | 1.441 (2) | C17—H17B | 0.96 |
C7—C8 | 1.426 (2) | C17—H17C | 0.96 |
C9—O1—C1 | 120.35 (11) | C11—C10—C15 | 117.37 (15) |
C5—O3—H3 | 109.5 | C11—C10—C9 | 121.11 (13) |
C3—O4—C16 | 118.12 (14) | C15—C10—C9 | 121.46 (14) |
C13—O5—C17 | 118.72 (13) | C12—C11—C10 | 122.24 (14) |
C2—C1—O1 | 116.89 (13) | C12—C11—H11 | 118.9 |
C2—C1—C6 | 122.80 (14) | C10—C11—H11 | 118.9 |
O1—C1—C6 | 120.31 (13) | C11—C12—C13 | 119.23 (14) |
C1—C2—C3 | 117.78 (14) | C11—C12—H12 | 120.4 |
C1—C2—H2 | 121.1 | C13—C12—H12 | 120.4 |
C3—C2—H2 | 121.1 | O5—C13—C12 | 124.69 (14) |
O4—C3—C2 | 114.83 (14) | O5—C13—C14 | 115.66 (13) |
O4—C3—C4 | 123.09 (15) | C12—C13—C14 | 119.65 (15) |
C2—C3—C4 | 122.08 (14) | C15—C14—C13 | 120.59 (14) |
C5—C4—C3 | 118.71 (15) | C15—C14—H14 | 119.7 |
C5—C4—H4 | 120.6 | C13—C14—H14 | 119.7 |
C3—C4—H4 | 120.6 | C14—C15—C10 | 120.92 (14) |
O3—C5—C4 | 119.48 (14) | C14—C15—H15 | 119.5 |
O3—C5—C6 | 119.26 (14) | C10—C15—H15 | 119.5 |
C4—C5—C6 | 121.25 (14) | O4—C16—H16A | 109.5 |
C1—C6—C5 | 117.37 (14) | O4—C16—H16B | 109.5 |
C1—C6—C7 | 120.18 (14) | H16A—C16—H16B | 109.5 |
C5—C6—C7 | 122.44 (13) | O4—C16—H16C | 109.5 |
O2—C7—C8 | 122.75 (14) | H16A—C16—H16C | 109.5 |
O2—C7—C6 | 121.62 (15) | H16B—C16—H16C | 109.5 |
C8—C7—C6 | 115.63 (13) | O5—C17—H17A | 109.5 |
C9—C8—C7 | 122.34 (14) | O5—C17—H17B | 109.5 |
C9—C8—H8 | 118.8 | H17A—C17—H17B | 109.5 |
C7—C8—H8 | 118.8 | O5—C17—H17C | 109.5 |
C8—C9—O1 | 121.16 (14) | H17A—C17—H17C | 109.5 |
C8—C9—C10 | 126.55 (14) | H17B—C17—H17C | 109.5 |
O1—C9—C10 | 112.28 (12) | ||
C9—O1—C1—C2 | 177.38 (14) | C5—C6—C7—C8 | −178.31 (15) |
C9—O1—C1—C6 | −1.6 (2) | O2—C7—C8—C9 | −178.69 (16) |
O1—C1—C2—C3 | −178.23 (14) | C6—C7—C8—C9 | 0.3 (2) |
C6—C1—C2—C3 | 0.7 (3) | C7—C8—C9—O1 | −1.7 (3) |
C16—O4—C3—C2 | −171.93 (16) | C7—C8—C9—C10 | 176.83 (16) |
C16—O4—C3—C4 | 7.7 (3) | C1—O1—C9—C8 | 2.4 (2) |
C1—C2—C3—O4 | 178.75 (15) | C1—O1—C9—C10 | −176.37 (13) |
C1—C2—C3—C4 | −0.9 (3) | C8—C9—C10—C11 | −3.7 (3) |
O4—C3—C4—C5 | −179.36 (16) | O1—C9—C10—C11 | 174.93 (14) |
C2—C3—C4—C5 | 0.3 (3) | C8—C9—C10—C15 | 179.17 (16) |
C3—C4—C5—O3 | 179.93 (16) | O1—C9—C10—C15 | −2.2 (2) |
C3—C4—C5—C6 | 0.6 (3) | C15—C10—C11—C12 | 0.9 (3) |
C2—C1—C6—C5 | 0.1 (2) | C9—C10—C11—C12 | −176.32 (15) |
O1—C1—C6—C5 | 179.00 (14) | C10—C11—C12—C13 | 0.1 (3) |
C2—C1—C6—C7 | −178.76 (16) | C17—O5—C13—C12 | −3.3 (3) |
O1—C1—C6—C7 | 0.1 (2) | C17—O5—C13—C14 | 176.77 (16) |
O3—C5—C6—C1 | 179.90 (15) | C11—C12—C13—O5 | 179.16 (16) |
C4—C5—C6—C1 | −0.8 (3) | C11—C12—C13—C14 | −0.9 (3) |
O3—C5—C6—C7 | −1.3 (3) | O5—C13—C14—C15 | −179.42 (15) |
C4—C5—C6—C7 | 178.07 (15) | C12—C13—C14—C15 | 0.6 (3) |
C1—C6—C7—O2 | 179.49 (15) | C13—C14—C15—C10 | 0.4 (3) |
C5—C6—C7—O2 | 0.7 (3) | C11—C10—C15—C14 | −1.1 (2) |
C1—C6—C7—C8 | 0.5 (2) | C9—C10—C15—C14 | 176.05 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 1.83 | 2.571 (2) | 149 |
C4—H4···O3i | 0.93 | 2.54 | 3.441 (2) | 163 |
C12—H12···O2ii | 0.93 | 2.52 | 3.430 (2) | 167 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |