Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007872/om2006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007872/om2006Isup2.hkl |
CCDC reference: 605146
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.097
- Data-to-parameter ratio = 9.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 - C18 .. 6.62 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 5.82 su
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 26.40 From the CIF: _reflns_number_total 2214 Count of symmetry unique reflns 2220 Completeness (_total/calc) 99.73% 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL and PLATON.
C24H22O2 | Dx = 1.219 Mg m−3 |
Mr = 342.42 | Melting point: 412 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4698 reflections |
a = 7.5637 (5) Å | θ = 1.9–26.4° |
b = 11.5604 (7) Å | µ = 0.08 mm−1 |
c = 21.3353 (13) Å | T = 295 K |
V = 1865.5 (2) Å3 | Prism, colorless |
Z = 4 | 0.38 × 0.20 × 0.14 mm |
F(000) = 728 |
Bruker SMART 1K CCD area-detector diffractometer | 2214 independent reflections |
Radiation source: fine-focus sealed tube | 1719 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −9→9 |
Tmin = 0.878, Tmax = 0.989 | k = −14→13 |
10849 measured reflections | l = −26→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.1176P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2214 reflections | Δρmax = 0.13 e Å−3 |
238 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
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) 7.4356 (0.0012) x + 2.0995 (0.0088) y - 0.5259 (0.0101) z = 1.1865 (0.0025) * 0.0046 (0.0018) C1 * 0.0154 (0.0019) C2 * 0.0040 (0.0019) C3 * -0.0120 (0.0022) C4 * -0.0097 (0.0024) C5 * 0.0023 (0.0023) C6 * 0.0145 (0.0022) C7 * 0.0034 (0.0024) C8 * -0.0085 (0.0021) C9 * -0.0139 (0.0018) C10 - 0.0480 (0.0026) O1 - 0.2914 (0.0040) C11 - 0.5643 (0.0052) C12 - 0.0392 (0.0033) C13 Rms deviation of fitted atoms = 0.0100 - 2.8374 (0.0031) x + 0.9911 (0.0083) y + 19.6924 (0.0043) z = 1.4447 (0.0015) Angle to previous plane (with approximate e.s.d.) = 67.92 (0.04) * -0.0109 (0.0016) C13 * -0.0183 (0.0018) C14 * 0.0085 (0.0018) C15 * 0.0181 (0.0021) C16 * -0.0044 (0.0022) C17 * -0.0059 (0.0020) C18 * -0.0097 (0.0020) C19 * 0.0036 (0.0020) C20 * 0.0155 (0.0020) C21 * 0.0035 (0.0018) C22 - 0.0003 (0.0025) O2 0.6768 (0.0036) C23 0.9882 (0.0046) C24 0.0214 (0.0030) C1 Rms deviation of fitted atoms = 0.0113 |
Refinement. Friedel pairs were merged before refinement. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1232 (2) | 0.10043 (13) | −0.02160 (7) | 0.0542 (4) | |
O2 | 0.4422 (2) | 0.04635 (15) | 0.13473 (7) | 0.0628 (5) | |
C1 | 0.1294 (3) | 0.13077 (17) | 0.08651 (9) | 0.0418 (5) | |
C2 | 0.1133 (3) | 0.20605 (18) | 0.13934 (10) | 0.0442 (5) | |
C3 | 0.1275 (3) | 0.1659 (2) | 0.20208 (10) | 0.0531 (6) | |
H3 | 0.1505 | 0.0881 | 0.2094 | 0.064* | |
C4 | 0.1084 (4) | 0.2385 (2) | 0.25157 (12) | 0.0657 (7) | |
H4 | 0.1177 | 0.2097 | 0.2921 | 0.079* | |
C5 | 0.0747 (4) | 0.3566 (2) | 0.24208 (13) | 0.0735 (8) | |
H5 | 0.0623 | 0.4059 | 0.2762 | 0.088* | |
C6 | 0.0604 (4) | 0.3983 (2) | 0.18325 (14) | 0.0697 (7) | |
H6 | 0.0379 | 0.4766 | 0.1774 | 0.084* | |
C7 | 0.0788 (3) | 0.32569 (19) | 0.13023 (12) | 0.0552 (6) | |
C8 | 0.0615 (4) | 0.3661 (2) | 0.06835 (12) | 0.0640 (7) | |
H8 | 0.0391 | 0.4442 | 0.0617 | 0.077* | |
C9 | 0.0763 (3) | 0.29544 (18) | 0.01820 (12) | 0.0569 (6) | |
H9 | 0.0644 | 0.3251 | −0.0221 | 0.068* | |
C10 | 0.1097 (3) | 0.17673 (18) | 0.02709 (10) | 0.0449 (5) | |
C11 | 0.0754 (4) | 0.1385 (2) | −0.08307 (11) | 0.0699 (7) | |
H11A | 0.1633 | 0.1919 | −0.0991 | 0.084* | |
H11B | −0.0380 | 0.1776 | −0.0820 | 0.084* | |
C12 | 0.0653 (6) | 0.0341 (3) | −0.12354 (13) | 0.1019 (11) | |
H12A | 0.1806 | 0.0000 | −0.1272 | 0.153* | |
H12B | 0.0234 | 0.0556 | −0.1644 | 0.153* | |
H12C | −0.0146 | −0.0209 | −0.1052 | 0.153* | |
C13 | 0.1598 (3) | 0.00437 (19) | 0.09562 (9) | 0.0427 (5) | |
C14 | 0.0258 (3) | −0.07740 (17) | 0.08004 (9) | 0.0447 (5) | |
C15 | −0.1413 (3) | −0.0444 (2) | 0.05567 (10) | 0.0515 (6) | |
H15 | −0.1649 | 0.0336 | 0.0489 | 0.062* | |
C16 | −0.2684 (4) | −0.1243 (2) | 0.04188 (11) | 0.0632 (7) | |
H16 | −0.3768 | −0.0999 | 0.0261 | 0.076* | |
C17 | −0.2381 (5) | −0.2416 (2) | 0.05099 (13) | 0.0716 (8) | |
H17 | −0.3247 | −0.2953 | 0.0405 | 0.086* | |
C18 | −0.0831 (5) | −0.2769 (2) | 0.07504 (12) | 0.0690 (8) | |
H18 | −0.0648 | −0.3555 | 0.0817 | 0.083* | |
C19 | 0.0539 (4) | −0.19761 (19) | 0.09059 (10) | 0.0541 (6) | |
C20 | 0.2150 (4) | −0.2322 (2) | 0.11621 (13) | 0.0690 (8) | |
H20 | 0.2352 | −0.3106 | 0.1231 | 0.083* | |
C21 | 0.3441 (4) | −0.1546 (2) | 0.13152 (12) | 0.0669 (8) | |
H21 | 0.4499 | −0.1802 | 0.1489 | 0.080* | |
C22 | 0.3164 (3) | −0.0350 (2) | 0.12089 (10) | 0.0523 (6) | |
C23 | 0.5574 (4) | 0.0219 (3) | 0.18695 (13) | 0.0787 (9) | |
H23A | 0.6503 | −0.0310 | 0.1742 | 0.094* | |
H23B | 0.4910 | −0.0138 | 0.2207 | 0.094* | |
C24 | 0.6353 (4) | 0.1329 (3) | 0.20840 (17) | 0.1045 (12) | |
H24A | 0.7045 | 0.1660 | 0.1752 | 0.157* | |
H24B | 0.7095 | 0.1191 | 0.2441 | 0.157* | |
H24C | 0.5423 | 0.1854 | 0.2197 | 0.157* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0689 (10) | 0.0558 (9) | 0.0380 (8) | 0.0021 (8) | −0.0019 (8) | 0.0086 (7) |
O2 | 0.0503 (9) | 0.0787 (11) | 0.0593 (10) | 0.0058 (10) | −0.0098 (8) | 0.0187 (9) |
C1 | 0.0420 (11) | 0.0417 (11) | 0.0419 (11) | 0.0012 (10) | −0.0005 (10) | 0.0057 (10) |
C2 | 0.0391 (11) | 0.0461 (12) | 0.0475 (12) | −0.0046 (10) | 0.0007 (10) | 0.0012 (9) |
C3 | 0.0526 (14) | 0.0607 (14) | 0.0460 (13) | −0.0017 (12) | 0.0025 (11) | 0.0011 (11) |
C4 | 0.0674 (18) | 0.0820 (18) | 0.0478 (13) | −0.0029 (16) | 0.0020 (12) | −0.0105 (13) |
C5 | 0.0778 (19) | 0.0720 (18) | 0.0706 (18) | −0.0048 (16) | 0.0021 (15) | −0.0262 (15) |
C6 | 0.0793 (17) | 0.0482 (14) | 0.0815 (19) | 0.0007 (15) | −0.0032 (16) | −0.0178 (13) |
C7 | 0.0523 (13) | 0.0462 (13) | 0.0670 (16) | −0.0023 (11) | −0.0023 (12) | −0.0016 (11) |
C8 | 0.0789 (18) | 0.0394 (12) | 0.0738 (18) | 0.0033 (13) | −0.0054 (15) | 0.0083 (12) |
C9 | 0.0640 (15) | 0.0504 (13) | 0.0562 (15) | −0.0017 (13) | −0.0064 (12) | 0.0160 (11) |
C10 | 0.0445 (12) | 0.0475 (12) | 0.0427 (11) | −0.0010 (11) | −0.0016 (10) | 0.0055 (10) |
C11 | 0.0831 (19) | 0.0834 (18) | 0.0432 (13) | 0.0114 (16) | −0.0111 (13) | 0.0100 (13) |
C12 | 0.139 (3) | 0.111 (3) | 0.0560 (17) | 0.023 (3) | −0.023 (2) | −0.0091 (17) |
C13 | 0.0485 (13) | 0.0453 (11) | 0.0343 (10) | 0.0066 (11) | 0.0048 (9) | 0.0059 (9) |
C14 | 0.0610 (14) | 0.0397 (11) | 0.0334 (11) | 0.0047 (11) | 0.0084 (10) | 0.0014 (9) |
C15 | 0.0607 (14) | 0.0449 (12) | 0.0488 (13) | −0.0049 (12) | −0.0003 (11) | 0.0015 (10) |
C16 | 0.0744 (17) | 0.0613 (15) | 0.0539 (14) | −0.0147 (14) | −0.0055 (13) | 0.0047 (12) |
C17 | 0.099 (2) | 0.0647 (18) | 0.0509 (15) | −0.0238 (17) | −0.0023 (15) | −0.0006 (13) |
C18 | 0.117 (3) | 0.0384 (12) | 0.0516 (14) | −0.0101 (16) | 0.0171 (17) | −0.0013 (11) |
C19 | 0.0789 (17) | 0.0433 (13) | 0.0400 (12) | 0.0094 (13) | 0.0101 (12) | 0.0042 (10) |
C20 | 0.097 (2) | 0.0458 (14) | 0.0646 (17) | 0.0184 (16) | 0.0120 (16) | 0.0122 (13) |
C21 | 0.0686 (17) | 0.0722 (18) | 0.0601 (16) | 0.0308 (16) | 0.0067 (13) | 0.0190 (14) |
C22 | 0.0529 (13) | 0.0598 (15) | 0.0442 (12) | 0.0098 (12) | 0.0033 (11) | 0.0086 (11) |
C23 | 0.0654 (16) | 0.108 (2) | 0.0628 (16) | 0.0114 (19) | −0.0185 (15) | 0.0162 (16) |
C24 | 0.080 (2) | 0.137 (3) | 0.097 (2) | −0.024 (2) | −0.0357 (19) | 0.023 (2) |
O1—C10 | 1.367 (3) | C12—H12B | 0.9600 |
O1—C11 | 1.430 (3) | C12—H12C | 0.9600 |
O2—C22 | 1.370 (3) | C13—C22 | 1.378 (3) |
O2—C23 | 1.443 (3) | C13—C14 | 1.426 (3) |
C1—C10 | 1.383 (3) | C14—C15 | 1.419 (3) |
C1—C2 | 1.429 (3) | C14—C19 | 1.424 (3) |
C1—C13 | 1.492 (3) | C15—C16 | 1.365 (3) |
C2—C3 | 1.421 (3) | C15—H15 | 0.9300 |
C2—C7 | 1.421 (3) | C16—C17 | 1.388 (4) |
C3—C4 | 1.356 (3) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.344 (4) |
C4—C5 | 1.403 (4) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.423 (4) |
C5—C6 | 1.349 (4) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.394 (4) |
C6—C7 | 1.415 (3) | C20—C21 | 1.366 (4) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.406 (3) | C21—C22 | 1.417 (4) |
C8—C9 | 1.351 (3) | C21—H21 | 0.9300 |
C8—H8 | 0.9300 | C23—C24 | 1.485 (4) |
C9—C10 | 1.408 (3) | C23—H23A | 0.9700 |
C9—H9 | 0.9300 | C23—H23B | 0.9700 |
C11—C12 | 1.486 (4) | C24—H24A | 0.9600 |
C11—H11A | 0.9700 | C24—H24B | 0.9600 |
C11—H11B | 0.9700 | C24—H24C | 0.9600 |
C12—H12A | 0.9600 | ||
C10—O1—C11 | 118.66 (18) | H12B—C12—H12C | 109.5 |
C22—O2—C23 | 116.9 (2) | C22—C13—C14 | 118.9 (2) |
C10—C1—C2 | 118.68 (18) | C22—C13—C1 | 120.4 (2) |
C10—C1—C13 | 120.83 (19) | C14—C13—C1 | 120.6 (2) |
C2—C1—C13 | 120.45 (18) | C15—C14—C19 | 117.0 (2) |
C3—C2—C7 | 117.4 (2) | C15—C14—C13 | 122.72 (19) |
C3—C2—C1 | 122.5 (2) | C19—C14—C13 | 120.3 (2) |
C7—C2—C1 | 120.03 (19) | C16—C15—C14 | 121.6 (2) |
C4—C3—C2 | 121.6 (2) | C16—C15—H15 | 119.2 |
C4—C3—H3 | 119.2 | C14—C15—H15 | 119.2 |
C2—C3—H3 | 119.2 | C15—C16—C17 | 121.0 (3) |
C3—C4—C5 | 120.6 (2) | C15—C16—H16 | 119.5 |
C3—C4—H4 | 119.7 | C17—C16—H16 | 119.5 |
C5—C4—H4 | 119.7 | C18—C17—C16 | 119.6 (3) |
C6—C5—C4 | 119.8 (2) | C18—C17—H17 | 120.2 |
C6—C5—H5 | 120.1 | C16—C17—H17 | 120.2 |
C4—C5—H5 | 120.1 | C17—C18—C19 | 121.9 (2) |
C5—C6—C7 | 121.6 (2) | C17—C18—H18 | 119.1 |
C5—C6—H6 | 119.2 | C19—C18—H18 | 119.1 |
C7—C6—H6 | 119.2 | C20—C19—C18 | 122.9 (2) |
C8—C7—C6 | 123.0 (2) | C20—C19—C14 | 118.2 (2) |
C8—C7—C2 | 118.0 (2) | C18—C19—C14 | 118.9 (3) |
C6—C7—C2 | 119.1 (2) | C21—C20—C19 | 122.0 (2) |
C9—C8—C7 | 122.3 (2) | C21—C20—H20 | 119.0 |
C9—C8—H8 | 118.8 | C19—C20—H20 | 119.0 |
C7—C8—H8 | 118.8 | C20—C21—C22 | 119.8 (3) |
C8—C9—C10 | 119.8 (2) | C20—C21—H21 | 120.1 |
C8—C9—H9 | 120.1 | C22—C21—H21 | 120.1 |
C10—C9—H9 | 120.1 | O2—C22—C13 | 117.1 (2) |
O1—C10—C1 | 116.16 (18) | O2—C22—C21 | 122.2 (2) |
O1—C10—C9 | 122.69 (19) | C13—C22—C21 | 120.8 (2) |
C1—C10—C9 | 121.1 (2) | O2—C23—C24 | 108.0 (2) |
O1—C11—C12 | 107.2 (2) | O2—C23—H23A | 110.1 |
O1—C11—H11A | 110.3 | C24—C23—H23A | 110.1 |
C12—C11—H11A | 110.3 | O2—C23—H23B | 110.1 |
O1—C11—H11B | 110.3 | C24—C23—H23B | 110.1 |
C12—C11—H11B | 110.3 | H23A—C23—H23B | 108.4 |
H11A—C11—H11B | 108.5 | C23—C24—H24A | 109.5 |
C11—C12—H12A | 109.5 | C23—C24—H24B | 109.5 |
C11—C12—H12B | 109.5 | H24A—C24—H24B | 109.5 |
H12A—C12—H12B | 109.5 | C23—C24—H24C | 109.5 |
C11—C12—H12C | 109.5 | H24A—C24—H24C | 109.5 |
H12A—C12—H12C | 109.5 | H24B—C24—H24C | 109.5 |
C10—C1—C2—C3 | 178.5 (2) | C10—C1—C13—C14 | −66.4 (3) |
C13—C1—C2—C3 | 0.9 (3) | C2—C1—C13—C14 | 111.3 (2) |
C10—C1—C2—C7 | −0.3 (3) | C22—C13—C14—C15 | 178.00 (19) |
C13—C1—C2—C7 | −178.0 (2) | C1—C13—C14—C15 | −0.2 (3) |
C7—C2—C3—C4 | 0.2 (3) | C22—C13—C14—C19 | 0.1 (3) |
C1—C2—C3—C4 | −178.7 (2) | C1—C13—C14—C19 | −178.16 (19) |
C2—C3—C4—C5 | −0.4 (4) | C19—C14—C15—C16 | −1.1 (3) |
C3—C4—C5—C6 | 0.3 (5) | C13—C14—C15—C16 | −179.1 (2) |
C4—C5—C6—C7 | −0.1 (5) | C14—C15—C16—C17 | −0.3 (4) |
C5—C6—C7—C8 | 178.8 (3) | C15—C16—C17—C18 | 1.5 (4) |
C5—C6—C7—C2 | −0.1 (4) | C16—C17—C18—C19 | −1.2 (4) |
C3—C2—C7—C8 | −179.0 (2) | C17—C18—C19—C20 | 179.3 (2) |
C1—C2—C7—C8 | 0.0 (3) | C17—C18—C19—C14 | −0.3 (4) |
C3—C2—C7—C6 | 0.0 (3) | C15—C14—C19—C20 | −178.2 (2) |
C1—C2—C7—C6 | 178.9 (2) | C13—C14—C19—C20 | −0.1 (3) |
C6—C7—C8—C9 | −178.8 (3) | C15—C14—C19—C18 | 1.4 (3) |
C2—C7—C8—C9 | 0.1 (4) | C13—C14—C19—C18 | 179.47 (19) |
C7—C8—C9—C10 | 0.2 (4) | C18—C19—C20—C21 | −179.2 (2) |
C11—O1—C10—C1 | 169.8 (2) | C14—C19—C20—C21 | 0.3 (4) |
C11—O1—C10—C9 | −9.7 (3) | C19—C20—C21—C22 | −0.5 (4) |
C2—C1—C10—O1 | −178.86 (18) | C23—O2—C22—C13 | 148.9 (2) |
C13—C1—C10—O1 | −1.2 (3) | C23—O2—C22—C21 | −31.4 (3) |
C2—C1—C10—C9 | 0.6 (3) | C14—C13—C22—O2 | 179.51 (18) |
C13—C1—C10—C9 | 178.3 (2) | C1—C13—C22—O2 | −2.3 (3) |
C8—C9—C10—O1 | 178.9 (2) | C14—C13—C22—C21 | −0.2 (3) |
C8—C9—C10—C1 | −0.6 (4) | C1—C13—C22—C21 | 178.0 (2) |
C10—O1—C11—C12 | −168.1 (2) | C20—C21—C22—O2 | −179.3 (2) |
C10—C1—C13—C22 | 115.5 (2) | C20—C21—C22—C13 | 0.4 (4) |
C2—C1—C13—C22 | −66.9 (3) | C22—O2—C23—C24 | −159.7 (2) |
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