Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701700X/rz2126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680701700X/rz2126Isup2.hkl |
CCDC reference: 648086
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.008 Å
- R factor = 0.069
- wR factor = 0.168
- Data-to-parameter ratio = 6.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.80 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.41 PLAT213_ALERT_2_C Atom C19 has ADP max/min Ratio ............. 3.30 prola PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.43 su PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C14 1.44 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
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 25.00 From the CIF: _reflns_number_total 1475 Count of symmetry unique reflns 1476 Completeness (_total/calc) 99.93% 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 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
Data collection: APEX2 (Bruker, 2005); cell refinement: 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).
C22H12O2 | Dx = 1.424 Mg m−3 |
Mr = 308.32 | Melting point = 527–528 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1475 reflections |
a = 6.7144 (4) Å | θ = 2.4–25.0° |
b = 12.6734 (7) Å | µ = 0.09 mm−1 |
c = 16.9009 (10) Å | T = 100 K |
V = 1438.17 (14) Å3 | Block, yellow |
Z = 4 | 0.26 × 0.13 × 0.08 mm |
F(000) = 640 |
Bruker SMART APEXII CCD area-detector diffractometer | 1475 independent reflections |
Radiation source: fine-focus sealed tube | 1190 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→15 |
Tmin = 0.977, Tmax = 0.993 | l = −16→20 |
9082 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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0719P)2 + 1.7541P] where P = (Fo2 + 2Fc2)/3 |
1475 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | 0.4467 (7) | 0.8817 (3) | 0.1298 (2) | 0.0334 (10) | |
O2 | 0.4748 (6) | 0.5795 (3) | −0.2196 (2) | 0.0316 (10) | |
C1 | 0.4437 (8) | 0.6036 (4) | 0.0706 (3) | 0.0230 (11) | |
C2 | 0.4455 (8) | 0.5028 (4) | 0.1077 (3) | 0.0241 (12) | |
H2A | 0.4515 | 0.4419 | 0.0771 | 0.029* | |
C3 | 0.4384 (9) | 0.4953 (4) | 0.1883 (3) | 0.0297 (13) | |
H3A | 0.4389 | 0.4292 | 0.2122 | 0.036* | |
C4 | 0.4303 (8) | 0.5855 (4) | 0.2349 (3) | 0.0269 (13) | |
H4A | 0.4241 | 0.5792 | 0.2896 | 0.032* | |
C5 | 0.4314 (8) | 0.6827 (4) | 0.2013 (3) | 0.0276 (13) | |
H5A | 0.4268 | 0.7423 | 0.2334 | 0.033* | |
C6 | 0.4394 (8) | 0.6946 (4) | 0.1186 (3) | 0.0226 (12) | |
C7 | 0.4406 (8) | 0.8042 (4) | 0.0861 (3) | 0.0254 (12) | |
C8 | 0.4396 (8) | 0.8157 (4) | −0.0011 (3) | 0.0218 (12) | |
C9 | 0.4362 (9) | 0.9130 (4) | −0.0417 (3) | 0.0247 (12) | |
H9A | 0.4319 | 0.9761 | −0.0136 | 0.030* | |
C10 | 0.4393 (9) | 0.9140 (4) | −0.1234 (3) | 0.0268 (13) | |
H10A | 0.4364 | 0.9786 | −0.1495 | 0.032* | |
C11 | 0.4464 (8) | 0.8219 (4) | −0.1680 (3) | 0.0216 (12) | |
H11A | 0.4502 | 0.8243 | −0.2230 | 0.026* | |
C12 | 0.4478 (9) | 0.7269 (4) | −0.1283 (3) | 0.0241 (12) | |
C13 | 0.4417 (8) | 0.7243 (4) | −0.0453 (3) | 0.0214 (12) | |
C14 | 0.4466 (9) | 0.6164 (4) | −0.0141 (3) | 0.0207 (11) | |
C15 | 0.4603 (8) | 0.5486 (4) | −0.0776 (3) | 0.0250 (12) | |
C16 | 0.4629 (8) | 0.6148 (4) | −0.1524 (3) | 0.0231 (12) | |
C17 | 0.4775 (10) | 0.4331 (4) | −0.0834 (3) | 0.0284 (13) | |
C18 | 0.3206 (11) | 0.3670 (5) | −0.0635 (4) | 0.0417 (17) | |
H18A | 0.2017 | 0.3942 | −0.0440 | 0.050* | |
C19 | 0.3468 (13) | 0.2566 (5) | −0.0739 (4) | 0.049 (2) | |
H19A | 0.2457 | 0.2101 | −0.0597 | 0.059* | |
C20 | 0.5241 (14) | 0.2181 (5) | −0.1053 (4) | 0.050 (2) | |
H20A | 0.5388 | 0.1461 | −0.1142 | 0.060* | |
C21 | 0.6732 (14) | 0.2839 (5) | −0.1229 (4) | 0.0487 (19) | |
H21A | 0.7930 | 0.2569 | −0.1416 | 0.058* | |
C22 | 0.6516 (11) | 0.3905 (5) | −0.1135 (4) | 0.0370 (15) | |
H22A | 0.7556 | 0.4351 | −0.1277 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.040 (2) | 0.029 (2) | 0.031 (2) | 0.007 (2) | −0.004 (2) | −0.0080 (17) |
O2 | 0.040 (2) | 0.032 (2) | 0.023 (2) | −0.002 (2) | −0.0003 (19) | −0.0026 (17) |
C1 | 0.013 (2) | 0.029 (3) | 0.027 (3) | −0.002 (3) | −0.003 (3) | 0.003 (2) |
C2 | 0.022 (3) | 0.022 (3) | 0.028 (3) | −0.002 (3) | 0.001 (3) | 0.000 (2) |
C3 | 0.032 (3) | 0.028 (3) | 0.030 (3) | −0.001 (3) | −0.001 (3) | 0.009 (2) |
C4 | 0.022 (3) | 0.040 (3) | 0.019 (3) | 0.004 (3) | −0.001 (3) | 0.006 (2) |
C5 | 0.020 (3) | 0.036 (3) | 0.027 (3) | −0.005 (3) | −0.002 (3) | −0.005 (3) |
C6 | 0.010 (3) | 0.035 (3) | 0.022 (2) | 0.001 (3) | −0.002 (2) | 0.007 (2) |
C7 | 0.018 (3) | 0.032 (3) | 0.026 (3) | −0.001 (3) | 0.002 (3) | −0.014 (3) |
C8 | 0.009 (2) | 0.023 (3) | 0.034 (3) | 0.001 (3) | 0.002 (3) | 0.006 (2) |
C9 | 0.018 (3) | 0.027 (3) | 0.028 (3) | −0.002 (3) | 0.004 (3) | 0.000 (2) |
C10 | 0.020 (3) | 0.026 (3) | 0.034 (3) | −0.006 (3) | 0.000 (3) | 0.002 (2) |
C11 | 0.014 (3) | 0.027 (3) | 0.023 (3) | −0.003 (3) | 0.002 (3) | 0.008 (2) |
C12 | 0.019 (3) | 0.031 (3) | 0.023 (3) | −0.004 (3) | −0.003 (3) | 0.000 (2) |
C13 | 0.009 (3) | 0.035 (3) | 0.020 (2) | −0.006 (3) | 0.000 (2) | 0.004 (2) |
C14 | 0.014 (3) | 0.022 (3) | 0.026 (3) | −0.002 (3) | 0.002 (3) | −0.001 (2) |
C15 | 0.021 (3) | 0.029 (3) | 0.025 (3) | −0.002 (3) | 0.000 (3) | 0.000 (2) |
C16 | 0.017 (3) | 0.028 (3) | 0.024 (3) | −0.005 (3) | 0.000 (3) | 0.003 (2) |
C17 | 0.044 (4) | 0.019 (3) | 0.021 (3) | −0.004 (3) | −0.003 (3) | −0.006 (2) |
C18 | 0.046 (4) | 0.042 (4) | 0.037 (4) | −0.013 (3) | −0.002 (3) | −0.010 (3) |
C19 | 0.087 (6) | 0.024 (4) | 0.036 (3) | −0.031 (4) | −0.010 (4) | 0.011 (3) |
C20 | 0.088 (6) | 0.026 (3) | 0.037 (4) | 0.008 (4) | −0.004 (4) | −0.015 (3) |
C21 | 0.084 (6) | 0.032 (4) | 0.030 (3) | 0.011 (4) | 0.008 (4) | −0.004 (3) |
C22 | 0.053 (4) | 0.027 (3) | 0.032 (3) | 0.003 (3) | 0.003 (3) | 0.004 (3) |
O1—C7 | 1.229 (6) | C10—H10A | 0.9300 |
O2—C16 | 1.223 (6) | C11—C12 | 1.377 (7) |
C1—C6 | 1.411 (7) | C11—H11A | 0.9300 |
C1—C2 | 1.424 (7) | C12—C13 | 1.405 (7) |
C1—C14 | 1.441 (7) | C12—C16 | 1.481 (7) |
C2—C3 | 1.365 (7) | C13—C14 | 1.466 (7) |
C2—H2A | 0.9300 | C14—C15 | 1.377 (7) |
C3—C4 | 1.389 (7) | C15—C17 | 1.471 (7) |
C3—H3A | 0.9300 | C15—C16 | 1.518 (7) |
C4—C5 | 1.357 (8) | C17—C22 | 1.384 (9) |
C4—H4A | 0.9300 | C17—C18 | 1.387 (9) |
C5—C6 | 1.407 (7) | C18—C19 | 1.422 (9) |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C6—C7 | 1.494 (7) | C19—C20 | 1.391 (11) |
C7—C8 | 1.480 (7) | C19—H19A | 0.9300 |
C8—C13 | 1.378 (7) | C20—C21 | 1.336 (10) |
C8—C9 | 1.412 (7) | C20—H20A | 0.9300 |
C9—C10 | 1.382 (7) | C21—C22 | 1.368 (9) |
C9—H9A | 0.9300 | C21—H21A | 0.9300 |
C10—C11 | 1.391 (7) | C22—H22A | 0.9300 |
C6—C1—C2 | 118.7 (5) | C11—C12—C13 | 120.4 (5) |
C6—C1—C14 | 118.6 (5) | C11—C12—C16 | 134.8 (4) |
C2—C1—C14 | 122.7 (5) | C13—C12—C16 | 104.7 (4) |
C3—C2—C1 | 120.1 (5) | C8—C13—C12 | 121.5 (5) |
C3—C2—H2A | 119.9 | C8—C13—C14 | 126.1 (4) |
C1—C2—H2A | 119.9 | C12—C13—C14 | 112.4 (5) |
C2—C3—C4 | 120.6 (5) | C15—C14—C1 | 134.7 (5) |
C2—C3—H3A | 119.7 | C15—C14—C13 | 107.7 (4) |
C4—C3—H3A | 119.7 | C1—C14—C13 | 117.5 (5) |
C5—C4—C3 | 120.7 (5) | C14—C15—C17 | 132.7 (5) |
C5—C4—H4A | 119.7 | C14—C15—C16 | 107.7 (4) |
C3—C4—H4A | 119.7 | C17—C15—C16 | 119.5 (5) |
C4—C5—C6 | 120.8 (5) | O2—C16—C12 | 127.6 (5) |
C4—C5—H5A | 119.6 | O2—C16—C15 | 124.9 (5) |
C6—C5—H5A | 119.6 | C12—C16—C15 | 107.5 (4) |
C5—C6—C1 | 119.0 (5) | C22—C17—C18 | 119.6 (5) |
C5—C6—C7 | 117.7 (5) | C22—C17—C15 | 118.6 (6) |
C1—C6—C7 | 123.3 (4) | C18—C17—C15 | 121.7 (6) |
O1—C7—C8 | 121.3 (5) | C17—C18—C19 | 118.1 (7) |
O1—C7—C6 | 121.5 (5) | C17—C18—H18A | 121.0 |
C8—C7—C6 | 117.2 (4) | C19—C18—H18A | 121.0 |
C13—C8—C9 | 118.1 (5) | C20—C19—C18 | 119.8 (6) |
C13—C8—C7 | 117.2 (5) | C20—C19—H19A | 120.1 |
C9—C8—C7 | 124.7 (5) | C18—C19—H19A | 120.1 |
C10—C9—C8 | 119.5 (5) | C21—C20—C19 | 120.5 (6) |
C10—C9—H9A | 120.2 | C21—C20—H20A | 119.8 |
C8—C9—H9A | 120.2 | C19—C20—H20A | 119.8 |
C9—C10—C11 | 122.3 (5) | C20—C21—C22 | 120.7 (8) |
C9—C10—H10A | 118.8 | C20—C21—H21A | 119.6 |
C11—C10—H10A | 118.8 | C22—C21—H21A | 119.6 |
C12—C11—C10 | 118.1 (4) | C21—C22—C17 | 121.1 (7) |
C12—C11—H11A | 121.0 | C21—C22—H22A | 119.4 |
C10—C11—H11A | 121.0 | C17—C22—H22A | 119.4 |
C6—C1—C2—C3 | 1.5 (8) | C6—C1—C14—C15 | 176.3 (6) |
C14—C1—C2—C3 | −178.6 (6) | C2—C1—C14—C15 | −3.6 (11) |
C1—C2—C3—C4 | −0.3 (10) | C6—C1—C14—C13 | −1.0 (8) |
C2—C3—C4—C5 | −0.7 (9) | C2—C1—C14—C13 | 179.2 (5) |
C3—C4—C5—C6 | 0.4 (9) | C8—C13—C14—C15 | −176.2 (5) |
C4—C5—C6—C1 | 0.8 (9) | C12—C13—C14—C15 | 1.3 (7) |
C4—C5—C6—C7 | −179.9 (5) | C8—C13—C14—C1 | 1.8 (9) |
C2—C1—C6—C5 | −1.8 (8) | C12—C13—C14—C1 | 179.2 (5) |
C14—C1—C6—C5 | 178.4 (5) | C1—C14—C15—C17 | 0.1 (12) |
C2—C1—C6—C7 | 179.0 (5) | C13—C14—C15—C17 | 177.5 (6) |
C14—C1—C6—C7 | −0.9 (8) | C1—C14—C15—C16 | −177.8 (6) |
C5—C6—C7—O1 | 4.4 (8) | C13—C14—C15—C16 | −0.4 (6) |
C1—C6—C7—O1 | −176.4 (5) | C11—C12—C16—O2 | −1.6 (12) |
C5—C6—C7—C8 | −177.2 (5) | C13—C12—C16—O2 | −179.0 (6) |
C1—C6—C7—C8 | 2.0 (8) | C11—C12—C16—C15 | 178.5 (6) |
O1—C7—C8—C13 | 177.1 (5) | C13—C12—C16—C15 | 1.2 (6) |
C6—C7—C8—C13 | −1.3 (7) | C14—C15—C16—O2 | 179.7 (6) |
O1—C7—C8—C9 | −3.0 (9) | C17—C15—C16—O2 | 1.4 (9) |
C6—C7—C8—C9 | 178.6 (5) | C14—C15—C16—C12 | −0.5 (6) |
C13—C8—C9—C10 | −1.3 (9) | C17—C15—C16—C12 | −178.8 (5) |
C7—C8—C9—C10 | 178.8 (5) | C14—C15—C17—C22 | −113.9 (7) |
C8—C9—C10—C11 | −0.3 (10) | C16—C15—C17—C22 | 63.9 (7) |
C9—C10—C11—C12 | 0.9 (9) | C14—C15—C17—C18 | 69.6 (9) |
C10—C11—C12—C13 | 0.1 (8) | C16—C15—C17—C18 | −112.7 (6) |
C10—C11—C12—C16 | −176.9 (7) | C22—C17—C18—C19 | 1.0 (9) |
C9—C8—C13—C12 | 2.3 (8) | C15—C17—C18—C19 | 177.5 (5) |
C7—C8—C13—C12 | −177.8 (5) | C17—C18—C19—C20 | −1.8 (10) |
C9—C8—C13—C14 | 179.6 (6) | C18—C19—C20—C21 | 2.8 (11) |
C7—C8—C13—C14 | −0.6 (8) | C19—C20—C21—C22 | −2.8 (11) |
C11—C12—C13—C8 | −1.7 (9) | C20—C21—C22—C17 | 2.0 (10) |
C16—C12—C13—C8 | 176.1 (5) | C18—C17—C22—C21 | −1.1 (9) |
C11—C12—C13—C14 | −179.3 (5) | C15—C17—C22—C21 | −177.7 (6) |
C16—C12—C13—C14 | −1.5 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19A···Cg1i | 0.93 | 3.11 | 3.814 (8) | 134 |
Symmetry code: (i) x−1/2, −y+1/2, −z. |
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