Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011986/bh2010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011986/bh2010Isup2.hkl |
CCDC reference: 608363
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.003 Å
- R factor = 0.053
- wR factor = 0.119
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found No errors found in this datablock checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ... # Comment Author's Contributions: # Comment Group-I: Planning of Experiment/Guidance: H.S.Y. Synthesis/Characterization/Crystallization/ Diagram preparation: H.G.A. & Y.B.B. |
Group-II: Data-collection/Structure Solution/Refinement: T.V. & T.N. Guidance/Report writing/Structure analysis: R.S.R # Comment
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) ans PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
C15H14O2 | Dx = 1.241 Mg m−3 |
Mr = 226.26 | Melting point: 343 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 805 reflections |
a = 8.582 (2) Å | θ = 3.1–22.8° |
b = 11.314 (3) Å | µ = 0.08 mm−1 |
c = 24.941 (7) Å | T = 295 K |
V = 2421.5 (12) Å3 | Cube, colourless |
Z = 8 | 0.34 × 0.31 × 0.25 mm |
F(000) = 960 |
Bruker SMART CCD area-detector diffractometer | 2380 independent reflections |
Radiation source: fine-focus sealed tube | 1630 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.960, Tmax = 0.988 | k = −13→13 |
17509 measured reflections | l = −30→30 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0423P)2 + 0.4398P] where P = (Fo2 + 2Fc2)/3 |
2380 reflections | (Δ/σ)max < 0.001 |
156 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Experimental. Ratio of minimum to maximum apparent transmission from SABABS was 0.893117 |
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. ====================================================================== Plane Calculations ====================================================================== Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = 0.74816(0.00047) m2 = 0.04405(0.00084) m3 = -0.66206(0.00051) D = -5.02878(0.00700) Atom d s d/s (d/s)**2 C7 * 0.0294 0.0020 14.767 218.069 C8 * -0.0253 0.0018 - 13.777 189.794 C9 * -0.0182 0.0019 - 9.418 88.706 C10 * 0.0195 0.0023 8.497 72.207 C11 * 0.0173 0.0025 6.804 46.288 C12 * 0.0020 0.0025 0.768 0.590 C13 * -0.0079 0.0021 - 3.696 13.659 O1 0.9005 0.0016 569.169 323953.844 ============ Sum((d/s)**2) for starred atoms 629.313 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity Plane 2 m1 = 0.67027(0.00038) m2 = -0.73904(0.00034) m3 = -0.06749(0.00032) D = -7.46508(0.00571) Atom d s d/s (d/s)**2 O2 * 0.0218 0.0015 14.832 219.981 C1 * 0.0230 0.0017 13.151 172.957 C2 * 0.0078 0.0017 4.481 20.079 C3 * 0.0023 0.0017 1.365 1.864 C4 * 0.0032 0.0018 1.718 2.950 C5 * -0.0168 0.0018 - 9.377 87.925 C6 * -0.0017 0.0017 - 0.999 0.998 C7 * -0.0171 0.0019 - 8.768 76.880 C14 * -0.0284 0.0020 - 13.859 192.063 C15 * -0.0240 0.0022 - 10.786 116.337 O1 - 0.1907 0.0015 - 123.187 15175.020 C8 0.1428 0.0019 74.774 5591.082 ============ Sum((d/s)**2) for starred atoms 892.034 Chi-squared at 95% for 7 degrees of freedom: 14.10 The group of atoms deviates significantly from planarity Plane 3 m1 = 0.66577(0.00058) m2 = -0.74371(0.00051) m3 = -0.06043(0.00074) D = -7.42604(0.01064) Atom d s d/s (d/s)**2 C1 * 0.0096 0.0017 5.495 30.198 C2 * -0.0071 0.0017 - 4.064 16.518 C3 * -0.0024 0.0017 - 1.408 1.982 C4 * 0.0108 0.0018 5.855 34.276 C5 * -0.0073 0.0018 - 4.064 16.516 C6 * -0.0027 0.0017 - 1.555 2.419 C7 - 0.0420 0.0019 - 21.528 463.434 O1 - 0.2263 0.0015 - 146.242 21386.867 ============ Sum((d/s)**2) for starred atoms 101.908 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 4 m1 = 0.75661(0.00058) m2 = 0.05375(0.00097) m3 = -0.65166(0.00067) D = -4.87460(0.00985) Atom d s d/s (d/s)**2 C8 * -0.0003 0.0018 - 0.165 0.027 C9 * -0.0055 0.0019 - 2.839 8.063 C10 * 0.0094 0.0023 4.077 16.624 C11 * -0.0034 0.0026 - 1.323 1.749 C12 * -0.0068 0.0026 - 2.669 7.126 C13 * 0.0062 0.0021 2.879 8.288 C7 0.0791 0.0020 39.770 1581.618 O1 0.9595 0.0016 605.852 367056.344 ============ Sum((d/s)**2) for starred atoms 41.876 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 5 m1 = 0.77072(0.00063) m2 = -0.63210(0.00076) m3 = -0.08024(0.00104) D = -6.41950(0.01300) Atom d s d/s (d/s)**2 O1 * -0.0009 0.0016 - 0.544 0.295 C1 * -0.0009 0.0018 - 0.509 0.259 C7 * 0.0035 0.0020 1.786 3.190 C8 * -0.0010 0.0019 - 0.530 0.281 C6 - 0.2153 0.0018 - 122.075 14902.340 ============ Sum((d/s)**2) for starred atoms 4.026 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 59.10 (0.05) 120.90 (0.05) 1 3 59.65 (0.06) 120.35 (0.06) 1 4 0.95 (0.06) 179.05 (0.06) 1 5 52.99 (0.07) 127.01 (0.07) 2 3 0.55 (0.05) 179.45 (0.05) 2 4 59.24 (0.06) 120.76 (0.06) 2 5 8.45 (0.05) 171.55 (0.05) 3 4 59.79 (0.06) 120.21 (0.06) 3 5 8.86 (0.05) 171.14 (0.05) 4 5 53.03 (0.08) 126.97 (0.08) ====================================================================== |
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 | 0.19280 (19) | 0.97690 (13) | 0.35447 (6) | 0.0740 (5) | |
O2 | 0.11439 (17) | 0.84840 (13) | 0.59858 (5) | 0.0613 (4) | |
C1 | 0.1109 (2) | 0.87921 (15) | 0.43303 (7) | 0.0401 (4) | |
C2 | 0.2119 (2) | 0.94389 (15) | 0.46572 (7) | 0.0434 (5) | |
H2 | 0.2816 | 0.9959 | 0.4496 | 0.052* | |
C3 | 0.2126 (2) | 0.93393 (15) | 0.52075 (7) | 0.0418 (5) | |
C4 | 0.1058 (2) | 0.85567 (16) | 0.54420 (7) | 0.0423 (5) | |
C5 | 0.0017 (2) | 0.79266 (15) | 0.51310 (7) | 0.0443 (5) | |
H5 | −0.0705 | 0.7426 | 0.5292 | 0.053* | |
C6 | 0.0052 (2) | 0.80438 (15) | 0.45792 (7) | 0.0423 (5) | |
H6 | −0.0646 | 0.7614 | 0.4371 | 0.051* | |
C7 | 0.1143 (2) | 0.89814 (17) | 0.37433 (8) | 0.0477 (5) | |
C8 | 0.0190 (2) | 0.82071 (17) | 0.33824 (7) | 0.0472 (5) | |
C9 | 0.0316 (2) | 0.69873 (18) | 0.33905 (7) | 0.0546 (5) | |
H9 | 0.0958 | 0.6624 | 0.3642 | 0.065* | |
C10 | −0.0505 (3) | 0.6308 (2) | 0.30276 (8) | 0.0711 (7) | |
H10 | −0.0397 | 0.5490 | 0.3029 | 0.085* | |
C11 | −0.1480 (3) | 0.6842 (3) | 0.26661 (9) | 0.0878 (9) | |
H11 | −0.2047 | 0.6382 | 0.2426 | 0.105* | |
C12 | −0.1624 (3) | 0.8048 (3) | 0.26558 (9) | 0.0895 (9) | |
H12 | −0.2290 | 0.8404 | 0.2410 | 0.107* | |
C13 | −0.0782 (3) | 0.8737 (2) | 0.30098 (8) | 0.0681 (7) | |
H13 | −0.0869 | 0.9556 | 0.2998 | 0.082* | |
C14 | 0.3212 (2) | 1.00539 (18) | 0.55519 (8) | 0.0597 (6) | |
H14A | 0.3917 | 0.9534 | 0.5735 | 0.090* | |
H14B | 0.2619 | 1.0494 | 0.5810 | 0.090* | |
H14C | 0.3793 | 1.0590 | 0.5330 | 0.090* | |
C15 | 0.0070 (3) | 0.77441 (19) | 0.62638 (8) | 0.0688 (6) | |
H15A | −0.0972 | 0.8023 | 0.6204 | 0.103* | |
H15B | 0.0295 | 0.7763 | 0.6641 | 0.103* | |
H15C | 0.0164 | 0.6948 | 0.6134 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0926 (12) | 0.0679 (10) | 0.0615 (9) | −0.0238 (9) | 0.0067 (8) | 0.0135 (8) |
O2 | 0.0668 (10) | 0.0746 (10) | 0.0425 (8) | −0.0077 (8) | −0.0013 (7) | −0.0015 (7) |
C1 | 0.0400 (11) | 0.0337 (9) | 0.0465 (10) | 0.0048 (8) | 0.0014 (8) | 0.0001 (8) |
C2 | 0.0383 (11) | 0.0366 (10) | 0.0553 (11) | 0.0005 (9) | 0.0028 (9) | 0.0035 (9) |
C3 | 0.0347 (10) | 0.0370 (10) | 0.0536 (11) | 0.0042 (8) | −0.0045 (9) | −0.0034 (8) |
C4 | 0.0445 (11) | 0.0423 (10) | 0.0401 (10) | 0.0088 (9) | −0.0003 (9) | −0.0042 (8) |
C5 | 0.0446 (11) | 0.0409 (10) | 0.0475 (11) | −0.0039 (9) | 0.0052 (9) | −0.0017 (8) |
C6 | 0.0419 (11) | 0.0384 (10) | 0.0464 (10) | −0.0019 (9) | −0.0021 (9) | −0.0054 (8) |
C7 | 0.0493 (12) | 0.0439 (11) | 0.0499 (11) | 0.0040 (10) | 0.0038 (9) | 0.0058 (9) |
C8 | 0.0450 (11) | 0.0607 (13) | 0.0359 (10) | 0.0025 (10) | 0.0040 (9) | 0.0019 (9) |
C9 | 0.0601 (13) | 0.0596 (13) | 0.0440 (11) | −0.0015 (11) | 0.0020 (10) | −0.0034 (10) |
C10 | 0.0804 (17) | 0.0793 (17) | 0.0535 (13) | −0.0154 (14) | 0.0112 (12) | −0.0159 (12) |
C11 | 0.0763 (19) | 0.139 (3) | 0.0483 (14) | −0.0290 (19) | −0.0035 (13) | −0.0180 (16) |
C12 | 0.0747 (18) | 0.139 (3) | 0.0543 (15) | 0.0034 (19) | −0.0176 (13) | 0.0081 (16) |
C13 | 0.0695 (15) | 0.0842 (17) | 0.0505 (12) | 0.0105 (13) | −0.0061 (12) | 0.0109 (12) |
C14 | 0.0540 (13) | 0.0585 (13) | 0.0667 (13) | −0.0052 (11) | −0.0138 (11) | −0.0056 (11) |
C15 | 0.0862 (17) | 0.0723 (15) | 0.0480 (12) | −0.0030 (14) | 0.0152 (12) | 0.0028 (11) |
O1—C7 | 1.222 (2) | C8—C13 | 1.385 (3) |
O2—C4 | 1.361 (2) | C9—C10 | 1.381 (3) |
O2—C15 | 1.425 (2) | C9—H9 | 0.9300 |
C1—C6 | 1.388 (2) | C10—C11 | 1.370 (3) |
C1—C2 | 1.397 (2) | C10—H10 | 0.9300 |
C1—C7 | 1.480 (3) | C11—C12 | 1.371 (4) |
C2—C3 | 1.377 (2) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.381 (3) |
C3—C4 | 1.402 (2) | C12—H12 | 0.9300 |
C3—C14 | 1.503 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.382 (2) | C14—H14A | 0.9600 |
C5—C6 | 1.383 (2) | C14—H14B | 0.9600 |
C5—H5 | 0.9300 | C14—H14C | 0.9600 |
C6—H6 | 0.9300 | C15—H15A | 0.9600 |
C7—C8 | 1.499 (3) | C15—H15B | 0.9600 |
C8—C9 | 1.384 (3) | C15—H15C | 0.9600 |
C4—O2—C15 | 119.04 (16) | C10—C9—H9 | 119.8 |
C6—C1—C2 | 117.66 (16) | C8—C9—H9 | 119.8 |
C6—C1—C7 | 122.92 (17) | C11—C10—C9 | 119.8 (3) |
C2—C1—C7 | 119.31 (16) | C11—C10—H10 | 120.1 |
C3—C2—C1 | 122.79 (17) | C9—C10—H10 | 120.1 |
C3—C2—H2 | 118.6 | C10—C11—C12 | 120.4 (2) |
C1—C2—H2 | 118.6 | C10—C11—H11 | 119.8 |
C2—C3—C4 | 117.70 (16) | C12—C11—H11 | 119.8 |
C2—C3—C14 | 121.87 (17) | C11—C12—C13 | 120.1 (2) |
C4—C3—C14 | 120.42 (17) | C11—C12—H12 | 119.9 |
O2—C4—C5 | 124.29 (17) | C13—C12—H12 | 119.9 |
O2—C4—C3 | 114.75 (16) | C12—C13—C8 | 120.0 (2) |
C5—C4—C3 | 120.95 (16) | C12—C13—H13 | 120.0 |
C4—C5—C6 | 119.68 (17) | C8—C13—H13 | 120.0 |
C4—C5—H5 | 120.2 | C3—C14—H14A | 109.5 |
C6—C5—H5 | 120.2 | C3—C14—H14B | 109.5 |
C5—C6—C1 | 121.18 (17) | H14A—C14—H14B | 109.5 |
C5—C6—H6 | 119.4 | C3—C14—H14C | 109.5 |
C1—C6—H6 | 119.4 | H14A—C14—H14C | 109.5 |
O1—C7—C1 | 121.16 (18) | H14B—C14—H14C | 109.5 |
O1—C7—C8 | 118.91 (17) | O2—C15—H15A | 109.5 |
C1—C7—C8 | 119.93 (16) | O2—C15—H15B | 109.5 |
C9—C8—C13 | 119.2 (2) | H15A—C15—H15B | 109.5 |
C9—C8—C7 | 122.07 (17) | O2—C15—H15C | 109.5 |
C13—C8—C7 | 118.60 (19) | H15A—C15—H15C | 109.5 |
C10—C9—C8 | 120.3 (2) | H15B—C15—H15C | 109.5 |
C6—C1—C2—C3 | 1.6 (3) | C2—C1—C7—O1 | −7.0 (3) |
C7—C1—C2—C3 | 178.00 (16) | C6—C1—C7—C8 | −10.2 (3) |
C1—C2—C3—C4 | −0.4 (3) | C2—C1—C7—C8 | 173.61 (16) |
C1—C2—C3—C14 | −179.36 (17) | O1—C7—C8—C9 | 125.7 (2) |
C15—O2—C4—C5 | −2.1 (3) | C1—C7—C8—C9 | −54.9 (3) |
C15—O2—C4—C3 | 177.78 (16) | O1—C7—C8—C13 | −50.7 (3) |
C2—C3—C4—O2 | 178.88 (16) | C1—C7—C8—C13 | 128.68 (19) |
C14—C3—C4—O2 | −2.2 (2) | C13—C8—C9—C10 | 0.7 (3) |
C2—C3—C4—C5 | −1.3 (3) | C7—C8—C9—C10 | −175.71 (18) |
C14—C3—C4—C5 | 177.68 (17) | C8—C9—C10—C11 | −1.6 (3) |
O2—C4—C5—C6 | −178.43 (17) | C9—C10—C11—C12 | 1.2 (4) |
C3—C4—C5—C6 | 1.7 (3) | C10—C11—C12—C13 | 0.2 (4) |
C4—C5—C6—C1 | −0.5 (3) | C11—C12—C13—C8 | −1.1 (4) |
C2—C1—C6—C5 | −1.1 (3) | C9—C8—C13—C12 | 0.7 (3) |
C7—C1—C6—C5 | −177.38 (16) | C7—C8—C13—C12 | 177.2 (2) |
C6—C1—C7—O1 | 169.17 (18) |
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