Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021403/rn6023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021403/rn6023Isup2.hkl |
CCDC reference: 252962
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.098
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.26 Deg.
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5556 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.26 Deg.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. CG .. 3.03 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. CG .. 2.95 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C4 .. CG .. 3.92 Ang.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 2000); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C16H12O2 | F(000) = 992 |
Mr = 236.26 | Dx = 1.335 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2391 reflections |
a = 15.5021 (19) Å | θ = 2.2–22.2° |
b = 6.6902 (8) Å | µ = 0.09 mm−1 |
c = 22.676 (3) Å | T = 298 K |
V = 2351.7 (5) Å3 | Block, yellow |
Z = 8 | 0.30 × 0.30 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 1684 independent reflections |
Radiation source: fine-focus sealed tube | 1377 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 100x100 microns pixels mm-1 | θmax = 23.3°, θmin = 1.8° |
ω scans | h = −17→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −6→7 |
Tmin = 0.974, Tmax = 0.991 | l = −25→25 |
9238 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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0514P)2 + 0.3759P] where P = (Fo2 + 2Fc2)/3 |
1684 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.11 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 | 0.67299 (9) | 0.7902 (2) | 0.38187 (6) | 0.0654 (4) | |
O2 | 0.56894 (8) | 0.22252 (17) | 0.47946 (5) | 0.0523 (4) | |
C1 | 0.65432 (11) | 0.6153 (3) | 0.39012 (7) | 0.0495 (5) | |
C2 | 0.64578 (11) | 0.5161 (3) | 0.44744 (7) | 0.0445 (4) | |
C3 | 0.63133 (12) | 0.2986 (3) | 0.43819 (7) | 0.0466 (5) | |
H3 | 0.6859 | 0.2260 | 0.4424 | 0.070* | |
C4 | 0.59852 (13) | 0.2808 (3) | 0.37518 (7) | 0.0545 (5) | |
H4A | 0.5360 | 0.2859 | 0.3741 | 0.082* | |
H4B | 0.6176 | 0.1566 | 0.3574 | 0.082* | |
C5 | 0.63751 (12) | 0.4604 (3) | 0.34323 (8) | 0.0550 (5) | |
H5A | 0.6908 | 0.4232 | 0.3237 | 0.082* | |
H5B | 0.5977 | 0.5116 | 0.3139 | 0.082* | |
C6 | 0.64313 (11) | 0.5923 (3) | 0.50187 (7) | 0.0468 (5) | |
H6 | 0.6548 | 0.7268 | 0.5084 | 0.056* | |
C7 | 0.62163 (10) | 0.4609 (2) | 0.55047 (7) | 0.0420 (4) | |
C8 | 0.62973 (11) | 0.5140 (3) | 0.61157 (7) | 0.0442 (4) | |
C9 | 0.67021 (12) | 0.6915 (3) | 0.63066 (8) | 0.0568 (5) | |
H9 | 0.6941 | 0.7778 | 0.6029 | 0.068* | |
C10 | 0.67492 (14) | 0.7385 (3) | 0.68899 (9) | 0.0672 (6) | |
H10 | 0.7017 | 0.8566 | 0.7005 | 0.081* | |
C11 | 0.64038 (14) | 0.6125 (3) | 0.73151 (8) | 0.0664 (6) | |
H11 | 0.6437 | 0.6470 | 0.7712 | 0.080* | |
C12 | 0.60178 (12) | 0.4389 (3) | 0.71512 (8) | 0.0576 (5) | |
H12 | 0.5793 | 0.3546 | 0.7439 | 0.069* | |
C13 | 0.59520 (11) | 0.3842 (3) | 0.65512 (7) | 0.0462 (5) | |
C14 | 0.55474 (12) | 0.2059 (3) | 0.63734 (8) | 0.0557 (5) | |
H14 | 0.5320 | 0.1209 | 0.6658 | 0.067* | |
C15 | 0.54805 (12) | 0.1552 (3) | 0.57984 (8) | 0.0549 (5) | |
H15 | 0.5207 | 0.0369 | 0.5691 | 0.066* | |
C16 | 0.58241 (11) | 0.2811 (3) | 0.53651 (7) | 0.0433 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0775 (10) | 0.0624 (10) | 0.0561 (8) | −0.0140 (7) | −0.0030 (7) | 0.0192 (7) |
O2 | 0.0670 (9) | 0.0530 (8) | 0.0369 (7) | −0.0174 (6) | 0.0032 (6) | −0.0023 (6) |
C1 | 0.0442 (11) | 0.0574 (12) | 0.0468 (10) | −0.0019 (9) | −0.0004 (8) | 0.0121 (9) |
C2 | 0.0430 (10) | 0.0508 (11) | 0.0398 (10) | −0.0053 (8) | −0.0018 (8) | 0.0050 (8) |
C3 | 0.0530 (11) | 0.0510 (11) | 0.0357 (9) | −0.0014 (8) | 0.0037 (8) | 0.0028 (8) |
C4 | 0.0705 (13) | 0.0548 (12) | 0.0384 (10) | 0.0005 (10) | −0.0012 (9) | −0.0009 (8) |
C5 | 0.0597 (12) | 0.0684 (13) | 0.0367 (10) | 0.0037 (10) | −0.0014 (8) | 0.0063 (9) |
C6 | 0.0505 (11) | 0.0435 (10) | 0.0464 (11) | −0.0087 (8) | −0.0019 (8) | 0.0009 (8) |
C7 | 0.0428 (10) | 0.0448 (10) | 0.0383 (9) | −0.0027 (8) | 0.0008 (8) | −0.0003 (8) |
C8 | 0.0439 (10) | 0.0479 (10) | 0.0407 (10) | 0.0018 (8) | −0.0019 (8) | −0.0027 (8) |
C9 | 0.0656 (13) | 0.0547 (12) | 0.0502 (11) | −0.0107 (10) | −0.0018 (9) | −0.0059 (9) |
C10 | 0.0797 (15) | 0.0660 (13) | 0.0558 (13) | −0.0094 (11) | −0.0070 (11) | −0.0186 (11) |
C11 | 0.0769 (15) | 0.0800 (16) | 0.0424 (11) | 0.0066 (12) | −0.0057 (10) | −0.0143 (11) |
C12 | 0.0669 (13) | 0.0679 (14) | 0.0381 (10) | 0.0038 (10) | 0.0017 (9) | −0.0003 (10) |
C13 | 0.0476 (11) | 0.0530 (11) | 0.0381 (9) | 0.0046 (9) | 0.0006 (8) | 0.0010 (9) |
C14 | 0.0681 (13) | 0.0557 (12) | 0.0434 (11) | −0.0081 (10) | 0.0053 (9) | 0.0088 (9) |
C15 | 0.0705 (13) | 0.0504 (11) | 0.0438 (10) | −0.0185 (10) | 0.0020 (9) | 0.0028 (9) |
C16 | 0.0488 (10) | 0.0462 (10) | 0.0348 (9) | −0.0033 (8) | −0.0008 (8) | −0.0016 (8) |
O1—C1 | 1.220 (2) | C7—C8 | 1.436 (2) |
O2—C16 | 1.368 (2) | C8—C9 | 1.411 (3) |
O2—C3 | 1.4388 (19) | C8—C13 | 1.419 (2) |
C1—C2 | 1.466 (2) | C9—C10 | 1.362 (3) |
C1—C5 | 1.507 (3) | C9—H9 | 0.9300 |
C2—C6 | 1.336 (2) | C10—C11 | 1.388 (3) |
C2—C3 | 1.487 (2) | C10—H10 | 0.9300 |
C3—C4 | 1.521 (2) | C11—C12 | 1.359 (3) |
C3—H3 | 0.9800 | C11—H11 | 0.9300 |
C4—C5 | 1.528 (3) | C12—C13 | 1.412 (2) |
C4—H4A | 0.9700 | C12—H12 | 0.9300 |
C4—H4B | 0.9700 | C13—C14 | 1.407 (3) |
C5—H5A | 0.9700 | C14—C15 | 1.351 (2) |
C5—H5B | 0.9700 | C14—H14 | 0.9300 |
C6—C7 | 1.449 (2) | C15—C16 | 1.400 (2) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—C16 | 1.384 (2) | ||
C16—O2—C3 | 114.26 (13) | C16—C7—C6 | 117.02 (15) |
O1—C1—C2 | 126.30 (17) | C8—C7—C6 | 124.32 (16) |
O1—C1—C5 | 126.32 (16) | C9—C8—C13 | 117.97 (16) |
C2—C1—C5 | 107.37 (16) | C9—C8—C7 | 122.89 (16) |
C6—C2—C1 | 130.48 (17) | C13—C8—C7 | 119.14 (15) |
C6—C2—C3 | 119.94 (15) | C10—C9—C8 | 121.05 (18) |
C1—C2—C3 | 109.38 (15) | C10—C9—H9 | 119.5 |
O2—C3—C2 | 110.84 (14) | C8—C9—H9 | 119.5 |
O2—C3—C4 | 110.99 (14) | C9—C10—C11 | 120.94 (19) |
C2—C3—C4 | 105.04 (14) | C9—C10—H10 | 119.5 |
O2—C3—H3 | 110.0 | C11—C10—H10 | 119.5 |
C2—C3—H3 | 110.0 | C12—C11—C10 | 119.93 (18) |
C4—C3—H3 | 110.0 | C12—C11—H11 | 120.0 |
C3—C4—C5 | 104.57 (14) | C10—C11—H11 | 120.0 |
C3—C4—H4A | 110.8 | C11—C12—C13 | 121.12 (18) |
C5—C4—H4A | 110.8 | C11—C12—H12 | 119.4 |
C3—C4—H4B | 110.8 | C13—C12—H12 | 119.4 |
C5—C4—H4B | 110.8 | C14—C13—C12 | 121.86 (17) |
H4A—C4—H4B | 108.9 | C14—C13—C8 | 119.16 (15) |
C1—C5—C4 | 105.93 (14) | C12—C13—C8 | 118.98 (17) |
C1—C5—H5A | 110.5 | C15—C14—C13 | 121.59 (17) |
C4—C5—H5A | 110.5 | C15—C14—H14 | 119.2 |
C1—C5—H5B | 110.5 | C13—C14—H14 | 119.2 |
C4—C5—H5B | 110.5 | C14—C15—C16 | 119.78 (17) |
H5A—C5—H5B | 108.7 | C14—C15—H15 | 120.1 |
C2—C6—C7 | 118.57 (16) | C16—C15—H15 | 120.1 |
C2—C6—H6 | 120.7 | O2—C16—C7 | 122.18 (15) |
C7—C6—H6 | 120.7 | O2—C16—C15 | 115.66 (15) |
C16—C7—C8 | 118.31 (15) | C7—C16—C15 | 121.98 (16) |
O1—C1—C2—C6 | 11.1 (3) | C13—C8—C9—C10 | −0.9 (3) |
C5—C1—C2—C6 | −169.97 (17) | C7—C8—C9—C10 | 178.57 (18) |
O1—C1—C2—C3 | −174.15 (17) | C8—C9—C10—C11 | 0.3 (3) |
C5—C1—C2—C3 | 4.76 (19) | C9—C10—C11—C12 | 0.5 (3) |
C16—O2—C3—C2 | −46.80 (19) | C10—C11—C12—C13 | −0.7 (3) |
C16—O2—C3—C4 | −163.13 (14) | C11—C12—C13—C14 | −179.40 (18) |
C6—C2—C3—O2 | 34.9 (2) | C11—C12—C13—C8 | 0.0 (3) |
C1—C2—C3—O2 | −140.44 (14) | C9—C8—C13—C14 | −179.80 (17) |
C6—C2—C3—C4 | 154.88 (16) | C7—C8—C13—C14 | 0.7 (2) |
C1—C2—C3—C4 | −20.49 (19) | C9—C8—C13—C12 | 0.8 (2) |
O2—C3—C4—C5 | 147.55 (15) | C7—C8—C13—C12 | −178.76 (16) |
C2—C3—C4—C5 | 27.71 (19) | C12—C13—C14—C15 | 179.48 (18) |
O1—C1—C5—C4 | −168.21 (18) | C8—C13—C14—C15 | 0.1 (3) |
C2—C1—C5—C4 | 12.88 (19) | C13—C14—C15—C16 | 0.4 (3) |
C3—C4—C5—C1 | −25.04 (19) | C3—O2—C16—C7 | 29.3 (2) |
C1—C2—C6—C7 | 171.10 (16) | C3—O2—C16—C15 | −155.43 (15) |
C3—C2—C6—C7 | −3.2 (2) | C8—C7—C16—O2 | 177.35 (15) |
C2—C6—C7—C16 | −17.4 (2) | C6—C7—C16—O2 | 3.9 (2) |
C2—C6—C7—C8 | 169.65 (16) | C8—C7—C16—C15 | 2.4 (3) |
C16—C7—C8—C9 | 178.63 (16) | C6—C7—C16—C15 | −171.00 (16) |
C6—C7—C8—C9 | −8.5 (3) | C14—C15—C16—O2 | −176.94 (17) |
C16—C7—C8—C13 | −1.9 (2) | C14—C15—C16—C7 | −1.7 (3) |
C6—C7—C8—C13 | 171.02 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O1i | 0.93 | 2.59 | 3.508 (2) | 172 |
C15—H15···O2ii | 0.93 | 2.48 | 3.388 (2) | 165 |
C4—H4A···Cgiii | 0.97 | 3.03 | 3.923 (2) | 154 |
C10—H10···Cgiv | 0.93 | 2.95 | 3.676 (2) | 136 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x+1, −y−1/2, z−1/2. |
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