The geometry of the 4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzo[
cd,
mn]pyrene system in the cationic state was established by X-ray structural resolution of the salts formed between the cation and various anions. The geometry was found to be planar for the 4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzo[
cd,
mn]pyrenylium and 2,6,10-tri(
tert-butyl)-4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzo[
cd,
mn]pyrenylium cations with the monovalent anions I
-, BF
, PF
, AsF
, HNO
3.NO
and CF
3SO
, and the divalent anions S
2O
and Mo
6Cl
. The salts were found to crystallize in distinct space groups following a characteristic pattern. Mixed cation-anion stacking resulted in space groups with high symmetry:
Pbca in three cases and
R3
c in one; a temperature study of the latter was made at ten different temperatures. The formation of dimers of anions and cations resulted in lower-symmetry space groups, mainly monoclinic (
P2
1/
n,
P2
1/
c and
C2/
c), but also
P1.
Supporting information
| Portable Document Format (PDF) file Supplementary material |
| Crystallographic Information File (CIF) Contains datablocks 3, 4, 5, 6120K, 7, 8, 9, 10, 11, 12, 6160K, 6198K, 6220K, 6243K, 6268K, 6293K, 6313K, 6338K, 6373K, global |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
| Structure factor file (SHELXL table format) Supplementary material |
CCDC references: 131774; 131775; 131776; 131777; 131778; 131779; 131780; 131781; 131782; 131783; 131784; 131785; 131786; 131787; 131788; 131789; 131790; 131791; 131792
For all compounds, data collection: SMART Siemens; cell refinement: SAINT Siemens; data reduction: SAINT Siemens. Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for (3), (4), (5), 6120K, (8), 6160K, 6198K, 6220K, 6243K, 6268K, 6293K, 6313K, 6338K, 6373K; SHELXS97 (Sheldrick, 1990) for (7), (9), (10), (11), (12). Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993) for (3), (4), (5), 6120K, (8), 6160K, 6198K, 6220K, 6243K, 6268K, 6293K, 6313K, 6338K, 6373K; SHELXL97 (Sheldrick, 1997) for (7), (9), (10), (11), (12). For all compounds, molecular graphics: SHELXTL (Sheldrick); software used to prepare material for publication: XCIF (Sheldrick).
(3) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium iodide
top
Crystal data top
C19H9O3·I | Z = 8 |
Mr = 412.16 | F(000) = 1600 |
Orthorhombic, Pbca | Dx = 1.810 Mg m−3 |
Hall symbol: -P 2ac 2ab | Mo Kα radiation, λ = 0.71073 Å |
a = 12.934 (3) Å | µ = 2.13 mm−1 |
b = 14.748 (3) Å | T = 293 K |
c = 15.858 (3) Å | Cube, dark red |
V = 3024.9 (10) Å3 | 0.32 × 0.30 × 0.30 mm |
Data collection top
Siemens SMART CCD diffractometer | 3093 independent reflections |
Radiation source: fine-focus sealed tube | 2679 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scan, frame data integration | θmax = 26.4°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) | h = −16→16 |
Tmin = 0.476, Tmax = 0.603 | k = −18→18 |
29370 measured reflections | l = −19→19 |
Refinement top
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.20 | Calculated w = 1/[σ2(Fo2) + (0.0552P)2 + 2.1435P] where P = (Fo2 + 2Fc2)/3 |
3093 reflections | (Δ/σ)max = 0.003 |
209 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −1.74 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8724 (2) | 0.6351 (2) | 0.7442 (2) | 0.0441 (7) | |
C2 | 0.9012 (3) | 0.5494 (2) | 0.7160 (2) | 0.0465 (7) | |
C3 | 0.9530 (3) | 0.5411 (3) | 0.6391 (2) | 0.0519 (8) | |
C4 | 0.9804 (4) | 0.4568 (3) | 0.6105 (2) | 0.0644 (10) | |
H4 | 1.0166 | 0.4498 | 0.5602 | 0.077* | |
C5 | 0.9525 (4) | 0.3824 (3) | 0.6584 (3) | 0.0641 (10) | |
H5 | 0.9697 | 0.3251 | 0.6383 | 0.077* | |
C6 | 0.9011 (3) | 0.3884 (3) | 0.7338 (3) | 0.0587 (9) | |
H6 | 0.8834 | 0.3364 | 0.7638 | 0.070* | |
C7 | 0.8763 (2) | 0.4731 (3) | 0.7639 (2) | 0.0512 (8) | |
C8 | 0.8207 (3) | 0.6440 (2) | 0.8205 (2) | 0.0476 (7) | |
C9 | 0.8002 (3) | 0.5673 (3) | 0.8695 (2) | 0.0541 (9) | |
C10 | 0.7532 (4) | 0.5760 (3) | 0.9466 (2) | 0.0687 (10) | |
H10 | 0.7396 | 0.5257 | 0.9802 | 0.082* | |
C11 | 0.7267 (3) | 0.6628 (4) | 0.9724 (3) | 0.0753 (12) | |
H11 | 0.6949 | 0.6692 | 1.0247 | 0.090* | |
C12 | 0.7441 (3) | 0.7402 (3) | 0.9260 (2) | 0.0650 (10) | |
H12 | 0.7242 | 0.7969 | 0.9459 | 0.078* | |
C13 | 0.7921 (3) | 0.7307 (3) | 0.8488 (2) | 0.0536 (8) | |
C14 | 0.8935 (2) | 0.7111 (2) | 0.6959 (2) | 0.0469 (7) | |
C15 | 0.8611 (3) | 0.7967 (3) | 0.7234 (2) | 0.0511 (8) | |
C16 | 0.8791 (3) | 0.8723 (2) | 0.6752 (3) | 0.0617 (10) | |
H16 | 0.8566 | 0.9293 | 0.6921 | 0.074* | |
C17 | 0.9324 (4) | 0.8600 (3) | 0.5997 (3) | 0.0645 (10) | |
H17 | 0.9463 | 0.9109 | 0.5671 | 0.077* | |
C18 | 0.9660 (3) | 0.7764 (3) | 0.5701 (2) | 0.0626 (10) | |
H18 | 1.0011 | 0.7713 | 0.5191 | 0.075* | |
C19 | 0.9454 (3) | 0.7018 (3) | 0.6186 (2) | 0.0531 (8) | |
O1 | 0.9754 (2) | 0.6168 (2) | 0.5923 (2) | 0.0605 (7) | |
O2 | 0.8272 (2) | 0.4824 (2) | 0.8404 (2) | 0.0581 (6) | |
O3 | 0.8128 (2) | 0.8055 (2) | 0.8003 (2) | 0.0579 (6) | |
I1 | 0.87640 (2) | 0.12899 (2) | 0.62911 (2) | 0.06149 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.038 (2) | 0.049 (2) | 0.046 (2) | −0.0013 (13) | −0.0049 (13) | −0.0001 (13) |
C2 | 0.047 (2) | 0.046 (2) | 0.046 (2) | −0.0021 (14) | −0.0040 (13) | −0.0022 (13) |
C3 | 0.057 (2) | 0.052 (2) | 0.047 (2) | 0.004 (2) | −0.0028 (15) | −0.0004 (14) |
C4 | 0.082 (3) | 0.061 (2) | 0.050 (2) | 0.012 (2) | −0.003 (2) | −0.010 (2) |
C5 | 0.070 (3) | 0.051 (2) | 0.071 (2) | 0.011 (2) | −0.017 (2) | −0.011 (2) |
C6 | 0.056 (2) | 0.047 (2) | 0.073 (2) | −0.005 (2) | −0.012 (2) | 0.004 (2) |
C7 | 0.047 (2) | 0.052 (2) | 0.055 (2) | −0.0044 (14) | −0.0076 (15) | 0.002 (2) |
C8 | 0.040 (2) | 0.056 (2) | 0.047 (2) | −0.0007 (14) | −0.0015 (13) | −0.0031 (14) |
C9 | 0.045 (2) | 0.066 (2) | 0.051 (2) | −0.005 (2) | −0.0004 (14) | 0.004 (2) |
C10 | 0.063 (2) | 0.085 (3) | 0.058 (2) | −0.003 (2) | 0.008 (2) | 0.011 (2) |
C11 | 0.065 (3) | 0.106 (4) | 0.055 (2) | 0.007 (3) | 0.011 (2) | −0.009 (2) |
C12 | 0.056 (2) | 0.079 (3) | 0.060 (2) | 0.008 (2) | 0.007 (2) | −0.014 (2) |
C13 | 0.043 (2) | 0.061 (2) | 0.056 (2) | 0.003 (2) | −0.0013 (15) | −0.006 (2) |
C14 | 0.043 (2) | 0.049 (2) | 0.049 (2) | −0.0015 (14) | −0.0016 (13) | 0.0013 (14) |
C15 | 0.046 (2) | 0.050 (2) | 0.057 (2) | −0.0021 (14) | −0.0043 (15) | 0.000 (2) |
C16 | 0.058 (2) | 0.048 (2) | 0.079 (3) | 0.002 (2) | −0.011 (2) | 0.003 (2) |
C17 | 0.064 (3) | 0.058 (2) | 0.072 (2) | −0.006 (2) | −0.009 (2) | 0.017 (2) |
C18 | 0.065 (2) | 0.066 (2) | 0.057 (2) | −0.003 (2) | 0.003 (2) | 0.014 (2) |
C19 | 0.054 (2) | 0.054 (2) | 0.051 (2) | 0.002 (2) | 0.0016 (15) | 0.0005 (15) |
O1 | 0.075 (2) | 0.0581 (15) | 0.0478 (13) | 0.0058 (13) | 0.0114 (12) | 0.0017 (11) |
O2 | 0.061 (2) | 0.0552 (14) | 0.0579 (14) | −0.0067 (12) | 0.0051 (12) | 0.0083 (11) |
O3 | 0.0576 (15) | 0.0519 (14) | 0.0641 (15) | 0.0071 (12) | 0.0032 (12) | −0.0067 (11) |
I1 | 0.0620 (2) | 0.0500 (2) | 0.0724 (2) | 0.00363 (10) | 0.00786 (11) | 0.01283 (10) |
Geometric parameters (Å, º) top
C1—C14 | 1.385 (5) | C9—O2 | 1.379 (5) |
C1—C8 | 1.388 (5) | C10—C11 | 1.387 (7) |
C1—C2 | 1.392 (5) | C11—C12 | 1.377 (6) |
C2—C7 | 1.396 (5) | C12—C13 | 1.379 (5) |
C2—C3 | 1.397 (5) | C13—O3 | 1.372 (5) |
C3—C4 | 1.371 (5) | C14—C15 | 1.400 (5) |
C3—O1 | 1.372 (4) | C14—C19 | 1.403 (5) |
C4—C5 | 1.382 (6) | C15—C16 | 1.371 (5) |
C5—C6 | 1.372 (7) | C15—O3 | 1.376 (4) |
C6—C7 | 1.376 (5) | C16—C17 | 1.393 (7) |
C7—O2 | 1.376 (4) | C17—C18 | 1.389 (6) |
C8—C9 | 1.398 (5) | C18—C19 | 1.368 (5) |
C8—C13 | 1.405 (5) | C19—O1 | 1.377 (4) |
C9—C10 | 1.371 (5) | | |
| | | |
C14—C1—C8 | 120.1 (3) | C9—C10—C11 | 117.3 (4) |
C14—C1—C2 | 120.3 (3) | C12—C11—C10 | 124.5 (4) |
C8—C1—C2 | 119.6 (3) | C11—C12—C13 | 117.6 (4) |
C1—C2—C7 | 119.7 (3) | O3—C13—C12 | 120.2 (3) |
C1—C2—C3 | 119.2 (3) | O3—C13—C8 | 120.1 (3) |
C7—C2—C3 | 121.1 (3) | C12—C13—C8 | 119.7 (4) |
C4—C3—O1 | 120.3 (3) | C1—C14—C15 | 119.8 (3) |
C4—C3—C2 | 119.5 (4) | C1—C14—C19 | 119.9 (3) |
O1—C3—C2 | 120.2 (3) | C15—C14—C19 | 120.3 (3) |
C3—C4—C5 | 118.1 (4) | C16—C15—O3 | 119.7 (4) |
C6—C5—C4 | 123.7 (4) | C16—C15—C14 | 120.5 (4) |
C5—C6—C7 | 118.3 (4) | O3—C15—C14 | 119.8 (3) |
O2—C7—C6 | 120.3 (3) | C15—C16—C17 | 117.2 (4) |
O2—C7—C2 | 120.4 (3) | C18—C17—C16 | 124.1 (4) |
C6—C7—C2 | 119.3 (3) | C19—C18—C17 | 117.5 (4) |
C1—C8—C9 | 120.0 (3) | C18—C19—O1 | 120.4 (3) |
C1—C8—C13 | 119.4 (3) | C18—C19—C14 | 120.4 (4) |
C9—C8—C13 | 120.6 (3) | O1—C19—C14 | 119.3 (3) |
C10—C9—O2 | 119.7 (4) | C3—O1—C19 | 121.1 (3) |
C10—C9—C8 | 120.3 (4) | C7—O2—C9 | 120.1 (3) |
O2—C9—C8 | 120.0 (3) | C13—O3—C15 | 120.7 (3) |
(4) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
tetrafluoroborate
top
Crystal data top
C19H9O3·BF4 | Z = 8 |
Mr = 372.07 | F(000) = 1504 |
Orthorhombic, Pbca | Dx = 1.648 Mg m−3 |
Hall symbol: -P 2ac 2ab | Mo Kα radiation, λ = 0.71073 Å |
a = 12.817 (3) Å | µ = 0.14 mm−1 |
b = 15.196 (3) Å | T = 120 K |
c = 15.396 (3) Å | Needle, orange |
V = 2998.6 (10) Å3 | 0.45 × 0.25 × 0.10 mm |
Data collection top
Siemens SMART CCD diffractometer | 3056 independent reflections |
Radiation source: fine-focus sealed tube | 2381 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scan, frame data integration | θmax = 26.4°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) | h = −16→16 |
Tmin = 0.871, Tmax = 0.980 | k = −18→18 |
29798 measured reflections | l = −19→19 |
Refinement top
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Calculated w = 1/[σ2(Fo2) + (0.0561P)2 + 2.684P] where P = (Fo2 + 2Fc2)/3 |
3054 reflections | (Δ/σ)max = −0.004 |
244 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 2 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.53697 (11) | 0.58286 (12) | 0.59875 (9) | 0.0571 (4) | |
F2 | 0.71216 (11) | 0.59357 (10) | 0.58733 (9) | 0.0483 (4) | |
F3 | 0.63652 (10) | 0.58242 (9) | 0.71954 (8) | 0.0418 (3) | |
F4 | 0.6204 (2) | 0.70674 (10) | 0.64035 (14) | 0.0853 (7) | |
O1 | 0.68793 (11) | 0.30995 (9) | 0.80019 (9) | 0.0301 (3) | |
O2 | 0.52205 (11) | 0.12281 (9) | 0.58920 (8) | 0.0286 (3) | |
O3 | 0.67891 (11) | −0.00380 (9) | 0.84489 (9) | 0.0300 (3) | |
B1 | 0.6263 (2) | 0.6169 (2) | 0.6367 (2) | 0.0302 (5) | |
C1 | 0.62937 (14) | 0.14304 (12) | 0.74483 (12) | 0.0240 (4) | |
C2 | 0.60645 (14) | 0.21643 (13) | 0.69395 (12) | 0.0247 (4) | |
C3 | 0.63884 (14) | 0.30015 (13) | 0.72109 (12) | 0.0264 (4) | |
C4 | 0.6192 (2) | 0.37264 (13) | 0.67007 (14) | 0.0305 (4) | |
H4 | 0.6411 | 0.4285 | 0.6869 | 0.037* | |
C5 | 0.5656 (2) | 0.35974 (13) | 0.59238 (13) | 0.0307 (5) | |
H5 | 0.5514 | 0.4086 | 0.5580 | 0.037* | |
C6 | 0.5321 (2) | 0.27747 (14) | 0.56355 (13) | 0.0293 (4) | |
H6 | 0.4967 | 0.2714 | 0.5112 | 0.035* | |
C7 | 0.55303 (15) | 0.20557 (13) | 0.61505 (12) | 0.0261 (4) | |
C8 | 0.60070 (14) | 0.05953 (13) | 0.71712 (12) | 0.0243 (4) | |
C9 | 0.54533 (15) | 0.05006 (13) | 0.63893 (12) | 0.0259 (4) | |
C10 | 0.5149 (2) | −0.03224 (14) | 0.61179 (13) | 0.0307 (5) | |
H10 | 0.4756 | −0.0395 | 0.5616 | 0.037* | |
C11 | 0.5448 (2) | −0.10424 (13) | 0.66169 (14) | 0.0314 (5) | |
H11 | 0.5264 | −0.1601 | 0.6424 | 0.038* | |
C12 | 0.6006 (2) | −0.09739 (13) | 0.73885 (14) | 0.0305 (5) | |
H12 | 0.6195 | −0.1472 | 0.7702 | 0.037* | |
C13 | 0.62709 (14) | −0.01423 (13) | 0.76747 (12) | 0.0267 (4) | |
C14 | 0.68214 (14) | 0.15331 (13) | 0.82334 (12) | 0.0259 (4) | |
C15 | 0.70531 (15) | 0.07872 (14) | 0.87366 (13) | 0.0283 (4) | |
C16 | 0.7550 (2) | 0.0885 (2) | 0.95264 (13) | 0.0340 (5) | |
H16 | 0.7711 | 0.0400 | 0.9870 | 0.041* | |
C17 | 0.7800 (2) | 0.1737 (2) | 0.97895 (13) | 0.0373 (5) | |
H17 | 0.8125 | 0.1808 | 1.0325 | 0.045* | |
C18 | 0.7594 (2) | 0.2488 (2) | 0.93008 (13) | 0.0337 (5) | |
H18 | 0.7782 | 0.3044 | 0.9499 | 0.040* | |
C19 | 0.71009 (15) | 0.23784 (14) | 0.85112 (12) | 0.0279 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0356 (7) | 0.0934 (12) | 0.0424 (8) | −0.0078 (8) | −0.0117 (6) | 0.0125 (8) |
F2 | 0.0386 (7) | 0.0632 (9) | 0.0430 (8) | 0.0050 (7) | 0.0037 (6) | −0.0017 (7) |
F3 | 0.0446 (8) | 0.0503 (8) | 0.0306 (6) | −0.0112 (6) | −0.0075 (6) | 0.0073 (6) |
F4 | 0.130 (2) | 0.0245 (8) | 0.1011 (15) | 0.0137 (9) | 0.0267 (13) | 0.0071 (8) |
O1 | 0.0288 (7) | 0.0320 (8) | 0.0296 (7) | −0.0031 (6) | −0.0012 (6) | −0.0057 (6) |
O2 | 0.0343 (8) | 0.0283 (7) | 0.0233 (7) | −0.0029 (6) | −0.0038 (6) | −0.0004 (6) |
O3 | 0.0284 (7) | 0.0337 (8) | 0.0279 (7) | 0.0039 (6) | −0.0010 (6) | 0.0036 (6) |
B1 | 0.0313 (12) | 0.0271 (11) | 0.0324 (12) | 0.0005 (9) | 0.0001 (10) | 0.0054 (9) |
C1 | 0.0194 (9) | 0.0294 (10) | 0.0233 (9) | 0.0017 (7) | 0.0034 (7) | −0.0021 (8) |
C2 | 0.0227 (9) | 0.0268 (10) | 0.0244 (9) | 0.0011 (7) | 0.0027 (7) | −0.0015 (8) |
C3 | 0.0218 (9) | 0.0311 (10) | 0.0262 (9) | 0.0004 (8) | 0.0031 (7) | −0.0043 (8) |
C4 | 0.0290 (10) | 0.0269 (10) | 0.0356 (11) | −0.0007 (8) | 0.0069 (9) | −0.0024 (9) |
C5 | 0.0302 (10) | 0.0296 (11) | 0.0323 (11) | 0.0033 (8) | 0.0060 (8) | 0.0048 (9) |
C6 | 0.0281 (10) | 0.0347 (11) | 0.0252 (9) | 0.0016 (8) | 0.0018 (8) | 0.0027 (8) |
C7 | 0.0245 (9) | 0.0299 (10) | 0.0238 (9) | −0.0019 (8) | 0.0026 (7) | −0.0036 (8) |
C8 | 0.0222 (9) | 0.0274 (10) | 0.0233 (9) | 0.0015 (7) | 0.0043 (7) | −0.0012 (8) |
C9 | 0.0275 (10) | 0.0275 (10) | 0.0226 (9) | 0.0010 (8) | 0.0045 (8) | −0.0017 (8) |
C10 | 0.0329 (11) | 0.0348 (11) | 0.0243 (9) | −0.0040 (9) | 0.0036 (8) | −0.0045 (8) |
C11 | 0.0331 (11) | 0.0272 (10) | 0.0340 (11) | −0.0036 (9) | 0.0111 (9) | −0.0056 (9) |
C12 | 0.0274 (10) | 0.0281 (10) | 0.0359 (11) | 0.0042 (8) | 0.0076 (8) | 0.0028 (9) |
C13 | 0.0213 (9) | 0.0323 (11) | 0.0265 (10) | 0.0034 (8) | 0.0051 (8) | 0.0010 (8) |
C14 | 0.0188 (9) | 0.0348 (11) | 0.0242 (9) | 0.0009 (8) | 0.0017 (7) | −0.0017 (8) |
C15 | 0.0211 (9) | 0.0378 (11) | 0.0260 (9) | 0.0017 (8) | 0.0032 (8) | 0.0004 (8) |
C16 | 0.0253 (10) | 0.0498 (13) | 0.0270 (10) | 0.0037 (9) | 0.0000 (8) | 0.0049 (9) |
C17 | 0.0251 (10) | 0.0625 (15) | 0.0245 (10) | −0.0032 (10) | −0.0032 (8) | −0.0022 (10) |
C18 | 0.0257 (10) | 0.0461 (12) | 0.0293 (10) | −0.0047 (9) | −0.0001 (8) | −0.0073 (9) |
C19 | 0.0214 (9) | 0.0359 (11) | 0.0265 (9) | −0.0006 (8) | 0.0027 (8) | −0.0023 (8) |
Geometric parameters (Å, º) top
F1—B1 | 1.386 (3) | C4—C5 | 1.394 (3) |
F2—B1 | 1.384 (3) | C5—C6 | 1.394 (3) |
F3—B1 | 1.385 (3) | C6—C7 | 1.376 (3) |
F4—B1 | 1.369 (3) | C8—C13 | 1.404 (3) |
O1—C19 | 1.377 (2) | C8—C9 | 1.405 (3) |
O1—C3 | 1.379 (2) | C9—C10 | 1.375 (3) |
O2—C9 | 1.377 (2) | C10—C11 | 1.391 (3) |
O2—C7 | 1.378 (2) | C11—C12 | 1.391 (3) |
O3—C15 | 1.372 (3) | C12—C13 | 1.381 (3) |
O3—C13 | 1.374 (2) | C14—C19 | 1.400 (3) |
C1—C8 | 1.388 (3) | C14—C15 | 1.405 (3) |
C1—C14 | 1.394 (3) | C15—C16 | 1.380 (3) |
C1—C2 | 1.394 (3) | C16—C17 | 1.395 (3) |
C2—C3 | 1.402 (3) | C17—C18 | 1.392 (3) |
C2—C7 | 1.404 (3) | C18—C19 | 1.380 (3) |
C3—C4 | 1.376 (3) | | |
| | | |
C19—O1—C3 | 120.7 (2) | C1—C8—C13 | 119.8 (2) |
C9—O2—C7 | 120.64 (15) | C1—C8—C9 | 119.4 (2) |
C15—O3—C13 | 120.3 (2) | C13—C8—C9 | 120.9 (2) |
F4—B1—F2 | 108.8 (2) | C10—C9—O2 | 120.0 (2) |
F4—B1—F3 | 110.2 (2) | C10—C9—C8 | 119.8 (2) |
F2—B1—F3 | 109.5 (2) | O2—C9—C8 | 120.2 (2) |
F4—B1—F1 | 110.1 (2) | C9—C10—C11 | 118.0 (2) |
F2—B1—F1 | 109.2 (2) | C10—C11—C12 | 123.7 (2) |
F3—B1—F1 | 109.0 (2) | C13—C12—C11 | 117.9 (2) |
C8—C1—C14 | 119.8 (2) | O3—C13—C12 | 120.1 (2) |
C8—C1—C2 | 120.2 (2) | O3—C13—C8 | 120.2 (2) |
C14—C1—C2 | 120.0 (2) | C12—C13—C8 | 119.7 (2) |
C1—C2—C3 | 119.7 (2) | C1—C14—C19 | 119.5 (2) |
C1—C2—C7 | 119.7 (2) | C1—C14—C15 | 119.4 (2) |
C3—C2—C7 | 120.6 (2) | C19—C14—C15 | 121.2 (2) |
C4—C3—O1 | 120.1 (2) | O3—C15—C16 | 119.7 (2) |
C4—C3—C2 | 120.2 (2) | O3—C15—C14 | 120.5 (2) |
O1—C3—C2 | 119.8 (2) | C16—C15—C14 | 119.8 (2) |
C3—C4—C5 | 117.9 (2) | C15—C16—C17 | 117.5 (2) |
C6—C5—C4 | 123.5 (2) | C18—C17—C16 | 124.1 (2) |
C7—C6—C5 | 117.9 (2) | C19—C18—C17 | 117.6 (2) |
C6—C7—O2 | 120.1 (2) | O1—C19—C18 | 120.0 (2) |
C6—C7—C2 | 120.0 (2) | O1—C19—C14 | 120.2 (2) |
O2—C7—C2 | 119.9 (2) | C18—C19—C14 | 119.8 (2) |
(5) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluoroarsenate
top
Crystal data top
C19H9O3·AsF6 | Z = 16 |
Mr = 474.18 | F(000) = 3744 |
Orthorhombic, Pbca | Dx = 1.827 Mg m−3 |
Hall symbol: -P 2ac 2ab | Mo Kα radiation, λ = 0.71073 Å |
a = 13.550 (3) Å | µ = 2.05 mm−1 |
b = 15.807 (3) Å | T = 293 K |
c = 32.201 (6) Å | Plate, orange |
V = 6897 (2) Å3 | 0.30 × 0.23 × 0.18 mm |
Data collection top
Siemens SMART CCD diffractometer | 7003 independent reflections |
Radiation source: fine-focus sealed tube | 4567 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω scan, frame data integration | θmax = 26.3°, θmin = 1.3° |
Absorption correction: empirical (using intensity measurements) | h = −16→16 |
Tmin = 0.404, Tmax = 0.603 | k = −19→19 |
69140 measured reflections | l = −40→40 |
Refinement top
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Calculated w = 1/[σ2(Fo2) + (0.0824P)2 + 14.1168P] where P = (Fo2 + 2Fc2)/3 |
7000 reflections | (Δ/σ)max = 0.376 |
523 parameters | Δρmax = 1.05 e Å−3 |
0 restraints | Δρmin = −0.97 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 3 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
As1 | 0.60399 (4) | 0.22916 (3) | 0.31861 (2) | 0.0437 (2) | |
F1 | 0.5238 (3) | 0.3152 (2) | 0.31736 (13) | 0.0792 (11) | |
F2 | 0.6881 (3) | 0.1470 (3) | 0.31872 (14) | 0.0949 (14) | |
F3 | 0.5041 (3) | 0.1599 (3) | 0.32144 (14) | 0.0912 (13) | |
F4 | 0.7005 (3) | 0.2992 (3) | 0.31359 (14) | 0.0941 (13) | |
F5 | 0.5989 (3) | 0.2223 (3) | 0.26548 (12) | 0.0956 (14) | |
F6 | 0.6123 (3) | 0.2389 (3) | 0.37213 (12) | 0.0969 (14) | |
As2 | 0.39514 (4) | 0.03844 (3) | 0.43634 (2) | 0.0498 (2) | |
F7 | 0.3975 (12) | 0.1003 (6) | 0.4764 (3) | 0.334 (9) | |
F8 | 0.3493 (4) | −0.0378 (3) | 0.4681 (2) | 0.149 (3) | |
F9 | 0.5065 (5) | −0.0003 (8) | 0.4437 (3) | 0.278 (7) | |
F10 | 0.4375 (5) | 0.1167 (4) | 0.4051 (2) | 0.165 (3) | |
F11 | 0.3951 (9) | −0.0211 (6) | 0.3967 (3) | 0.275 (6) | |
F12 | 0.2850 (5) | 0.0754 (6) | 0.4286 (3) | 0.244 (6) | |
O1 | 0.2888 (3) | 0.1032 (3) | 0.2914 (2) | 0.0763 (14) | |
O2 | 0.3340 (3) | 0.4058 (3) | 0.28354 (14) | 0.0694 (12) | |
O3 | 0.4597 (3) | 0.2254 (2) | 0.17558 (12) | 0.0591 (11) | |
C1 | 0.3605 (4) | 0.2449 (4) | 0.2502 (2) | 0.0462 (12) | |
C2 | 0.3097 (4) | 0.2547 (4) | 0.2877 (2) | 0.0567 (15) | |
C3 | 0.2751 (4) | 0.1818 (6) | 0.3080 (2) | 0.073 (2) | |
C4 | 0.2282 (6) | 0.1925 (8) | 0.3464 (3) | 0.100 (3) | |
H4 | 0.2045 | 0.1461 | 0.3610 | 0.119* | |
C5 | 0.2179 (7) | 0.2734 (9) | 0.3619 (3) | 0.114 (4) | |
H5 | 0.1868 | 0.2798 | 0.3875 | 0.137* | |
C6 | 0.2511 (6) | 0.3465 (6) | 0.3417 (3) | 0.096 (3) | |
H6 | 0.2421 | 0.4000 | 0.3532 | 0.115* | |
C7 | 0.2981 (4) | 0.3353 (5) | 0.3039 (2) | 0.066 (2) | |
C8 | 0.3967 (4) | 0.3158 (3) | 0.2296 (2) | 0.0451 (12) | |
C9 | 0.3828 (4) | 0.3965 (4) | 0.2467 (2) | 0.0560 (15) | |
C10 | 0.4167 (5) | 0.4664 (4) | 0.2249 (2) | 0.069 (2) | |
H10 | 0.4066 | 0.5207 | 0.2350 | 0.083* | |
C11 | 0.4652 (5) | 0.4541 (4) | 0.1882 (2) | 0.070 (2) | |
H11 | 0.4892 | 0.5012 | 0.1742 | 0.084* | |
C12 | 0.4806 (5) | 0.3744 (4) | 0.1706 (2) | 0.064 (2) | |
H12 | 0.5132 | 0.3685 | 0.1453 | 0.076* | |
C13 | 0.4464 (4) | 0.3053 (3) | 0.1917 (2) | 0.0484 (13) | |
C14 | 0.3748 (4) | 0.1648 (4) | 0.2338 (2) | 0.0498 (13) | |
C15 | 0.4250 (5) | 0.1551 (4) | 0.1964 (2) | 0.0559 (14) | |
C16 | 0.4380 (6) | 0.0761 (4) | 0.1792 (2) | 0.073 (2) | |
H16 | 0.4703 | 0.0689 | 0.1540 | 0.088* | |
C17 | 0.4013 (6) | 0.0085 (4) | 0.2009 (3) | 0.083 (2) | |
H17 | 0.4106 | −0.0451 | 0.1898 | 0.100* | |
C18 | 0.3520 (6) | 0.0143 (4) | 0.2378 (3) | 0.080 (2) | |
H18 | 0.3286 | −0.0339 | 0.2512 | 0.096* | |
C19 | 0.3375 (4) | 0.0941 (4) | 0.2549 (2) | 0.059 (2) | |
O4 | 0.1946 (3) | −0.1254 (3) | 0.52441 (13) | 0.0583 (10) | |
O5 | 0.1788 (3) | 0.1755 (3) | 0.54636 (13) | 0.0678 (12) | |
O6 | 0.0359 (3) | 0.0532 (2) | 0.42312 (12) | 0.0561 (10) | |
C20 | 0.1374 (4) | 0.0342 (3) | 0.4978 (2) | 0.0431 (12) | |
C21 | 0.1871 (4) | 0.0247 (4) | 0.5357 (2) | 0.0474 (13) | |
C22 | 0.2130 (4) | −0.0567 (4) | 0.5488 (2) | 0.0571 (15) | |
C23 | 0.2571 (6) | −0.0663 (5) | 0.5871 (2) | 0.078 (2) | |
H23 | 0.2749 | −0.1196 | 0.5967 | 0.094* | |
C24 | 0.2743 (6) | 0.0049 (7) | 0.6109 (2) | 0.092 (3) | |
H24 | 0.3037 | −0.0022 | 0.6368 | 0.111* | |
C25 | 0.2505 (6) | 0.0858 (6) | 0.5985 (2) | 0.086 (2) | |
H25 | 0.2643 | 0.1321 | 0.6153 | 0.103* | |
C26 | 0.2054 (5) | 0.0962 (4) | 0.5603 (2) | 0.062 (2) | |
C27 | 0.1075 (4) | 0.1153 (3) | 0.4848 (2) | 0.0449 (12) | |
C28 | 0.1280 (4) | 0.1858 (4) | 0.5097 (2) | 0.0560 (15) | |
C29 | 0.0964 (5) | 0.2645 (4) | 0.4968 (3) | 0.073 (2) | |
H29 | 0.1097 | 0.3124 | 0.5127 | 0.087* | |
C30 | 0.0449 (6) | 0.2709 (4) | 0.4601 (2) | 0.072 (2) | |
H30 | 0.0233 | 0.3241 | 0.4518 | 0.086* | |
C31 | 0.0237 (5) | 0.2024 (4) | 0.4350 (2) | 0.066 (2) | |
H31 | −0.0113 | 0.2094 | 0.4104 | 0.079* | |
C32 | 0.0558 (4) | 0.1234 (3) | 0.4474 (2) | 0.0476 (13) | |
C33 | 0.1168 (4) | −0.0358 (3) | 0.4735 (2) | 0.0422 (12) | |
C34 | 0.0663 (4) | −0.0267 (3) | 0.4361 (2) | 0.0503 (13) | |
C35 | 0.0475 (5) | −0.0956 (4) | 0.4118 (2) | 0.066 (2) | |
H35 | 0.0155 | −0.0897 | 0.3864 | 0.079* | |
C36 | 0.0770 (5) | −0.1739 (4) | 0.4258 (2) | 0.072 (2) | |
H36 | 0.0621 | −0.2210 | 0.4097 | 0.086* | |
C37 | 0.1275 (5) | −0.1861 (4) | 0.4625 (2) | 0.066 (2) | |
H37 | 0.1482 | −0.2398 | 0.4705 | 0.079* | |
C38 | 0.1466 (4) | −0.1165 (3) | 0.4871 (2) | 0.0495 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
As1 | 0.0423 (3) | 0.0421 (3) | 0.0466 (3) | 0.0021 (2) | 0.0044 (2) | −0.0035 (2) |
F1 | 0.076 (3) | 0.048 (2) | 0.114 (3) | 0.012 (2) | 0.006 (2) | 0.004 (2) |
F2 | 0.072 (3) | 0.094 (3) | 0.119 (3) | 0.041 (2) | 0.009 (2) | 0.001 (3) |
F3 | 0.080 (3) | 0.065 (2) | 0.129 (4) | −0.013 (2) | 0.002 (2) | −0.001 (2) |
F4 | 0.066 (3) | 0.099 (3) | 0.118 (3) | −0.030 (2) | 0.018 (2) | −0.018 (3) |
F5 | 0.105 (3) | 0.133 (4) | 0.049 (2) | −0.005 (3) | 0.009 (2) | −0.003 (2) |
F6 | 0.088 (3) | 0.145 (4) | 0.057 (2) | 0.003 (3) | −0.003 (2) | −0.015 (3) |
As2 | 0.0546 (4) | 0.0400 (3) | 0.0547 (4) | −0.0046 (3) | 0.0126 (3) | −0.0005 (2) |
F7 | 0.67 (3) | 0.159 (8) | 0.170 (8) | −0.142 (11) | 0.008 (11) | −0.070 (6) |
F8 | 0.110 (4) | 0.099 (4) | 0.237 (7) | 0.024 (3) | 0.087 (4) | 0.087 (4) |
F9 | 0.081 (4) | 0.432 (15) | 0.321 (12) | 0.020 (7) | 0.044 (6) | 0.244 (12) |
F10 | 0.169 (6) | 0.128 (5) | 0.197 (6) | 0.004 (4) | 0.078 (5) | 0.089 (4) |
F11 | 0.405 (17) | 0.232 (9) | 0.187 (8) | −0.089 (10) | 0.079 (9) | −0.149 (8) |
F12 | 0.101 (5) | 0.369 (12) | 0.262 (9) | 0.103 (6) | 0.093 (5) | 0.232 (9) |
O1 | 0.057 (3) | 0.089 (4) | 0.083 (3) | −0.013 (3) | −0.001 (2) | 0.039 (3) |
O2 | 0.062 (3) | 0.078 (3) | 0.068 (3) | 0.029 (2) | −0.005 (2) | −0.010 (2) |
O3 | 0.074 (3) | 0.049 (2) | 0.054 (2) | −0.005 (2) | 0.010 (2) | 0.003 (2) |
C1 | 0.038 (3) | 0.056 (3) | 0.045 (3) | −0.001 (2) | −0.005 (2) | 0.010 (3) |
C2 | 0.038 (3) | 0.082 (4) | 0.050 (3) | 0.011 (3) | 0.001 (2) | 0.015 (3) |
C3 | 0.040 (3) | 0.117 (6) | 0.062 (4) | −0.002 (4) | 0.002 (3) | 0.028 (4) |
C4 | 0.054 (4) | 0.168 (9) | 0.077 (5) | 0.001 (5) | 0.013 (4) | 0.046 (6) |
C5 | 0.068 (5) | 0.209 (13) | 0.064 (5) | 0.029 (7) | 0.019 (4) | 0.009 (7) |
C6 | 0.071 (5) | 0.143 (8) | 0.074 (5) | 0.035 (5) | 0.006 (4) | −0.008 (5) |
C7 | 0.045 (3) | 0.100 (5) | 0.054 (3) | 0.023 (4) | −0.001 (3) | 0.003 (4) |
C8 | 0.040 (3) | 0.048 (3) | 0.047 (3) | 0.002 (2) | −0.006 (2) | 0.002 (2) |
C9 | 0.053 (4) | 0.054 (3) | 0.061 (4) | 0.012 (3) | −0.007 (3) | 0.000 (3) |
C10 | 0.078 (5) | 0.040 (3) | 0.091 (5) | 0.008 (3) | −0.020 (4) | 0.001 (3) |
C11 | 0.064 (4) | 0.048 (4) | 0.099 (5) | −0.005 (3) | −0.008 (4) | 0.021 (4) |
C12 | 0.068 (4) | 0.060 (4) | 0.063 (4) | −0.006 (3) | 0.004 (3) | 0.017 (3) |
C13 | 0.053 (3) | 0.041 (3) | 0.050 (3) | 0.002 (2) | −0.002 (3) | 0.007 (2) |
C14 | 0.045 (3) | 0.048 (3) | 0.056 (3) | −0.008 (2) | −0.009 (2) | 0.013 (3) |
C15 | 0.060 (4) | 0.050 (3) | 0.058 (3) | −0.001 (3) | −0.007 (3) | 0.003 (3) |
C16 | 0.095 (5) | 0.050 (4) | 0.075 (4) | −0.004 (4) | −0.004 (4) | −0.006 (3) |
C17 | 0.097 (6) | 0.048 (4) | 0.105 (6) | −0.005 (4) | −0.017 (5) | −0.006 (4) |
C18 | 0.077 (5) | 0.049 (4) | 0.115 (6) | −0.021 (3) | −0.031 (5) | 0.028 (4) |
C19 | 0.042 (3) | 0.065 (4) | 0.071 (4) | −0.013 (3) | −0.011 (3) | 0.025 (3) |
O4 | 0.051 (2) | 0.057 (2) | 0.066 (3) | 0.006 (2) | 0.000 (2) | 0.010 (2) |
O5 | 0.067 (3) | 0.071 (3) | 0.066 (3) | −0.002 (2) | 0.000 (2) | −0.025 (2) |
O6 | 0.064 (3) | 0.054 (2) | 0.050 (2) | 0.001 (2) | −0.007 (2) | 0.002 (2) |
C20 | 0.036 (3) | 0.046 (3) | 0.047 (3) | −0.001 (2) | 0.008 (2) | −0.004 (2) |
C21 | 0.035 (3) | 0.062 (3) | 0.046 (3) | −0.001 (2) | 0.004 (2) | −0.006 (3) |
C22 | 0.043 (3) | 0.080 (4) | 0.049 (3) | 0.007 (3) | 0.001 (3) | 0.009 (3) |
C23 | 0.066 (4) | 0.101 (6) | 0.069 (4) | 0.016 (4) | −0.005 (4) | 0.013 (4) |
C24 | 0.071 (5) | 0.147 (8) | 0.060 (4) | 0.015 (5) | −0.016 (4) | −0.002 (5) |
C25 | 0.079 (5) | 0.117 (7) | 0.061 (4) | 0.007 (5) | −0.014 (4) | −0.026 (4) |
C26 | 0.052 (4) | 0.079 (4) | 0.055 (4) | 0.004 (3) | 0.003 (3) | −0.013 (3) |
C27 | 0.038 (3) | 0.048 (3) | 0.050 (3) | 0.000 (2) | 0.010 (2) | −0.003 (2) |
C28 | 0.053 (3) | 0.052 (3) | 0.063 (4) | −0.005 (3) | 0.016 (3) | −0.011 (3) |
C29 | 0.078 (5) | 0.043 (3) | 0.098 (5) | −0.007 (3) | 0.020 (4) | −0.014 (3) |
C30 | 0.079 (5) | 0.047 (4) | 0.091 (5) | 0.005 (3) | 0.014 (4) | 0.015 (4) |
C31 | 0.073 (4) | 0.057 (4) | 0.067 (4) | 0.003 (3) | 0.010 (3) | 0.016 (3) |
C32 | 0.049 (3) | 0.041 (3) | 0.052 (3) | −0.003 (2) | 0.010 (3) | 0.007 (2) |
C33 | 0.037 (3) | 0.042 (3) | 0.048 (3) | −0.003 (2) | 0.005 (2) | 0.002 (2) |
C34 | 0.050 (3) | 0.041 (3) | 0.059 (3) | −0.005 (2) | 0.002 (3) | 0.001 (3) |
C35 | 0.066 (4) | 0.072 (4) | 0.059 (4) | −0.010 (3) | −0.010 (3) | −0.010 (3) |
C36 | 0.074 (5) | 0.054 (4) | 0.087 (5) | −0.008 (3) | 0.001 (4) | −0.022 (4) |
C37 | 0.064 (4) | 0.043 (3) | 0.091 (5) | −0.001 (3) | 0.008 (3) | −0.006 (3) |
C38 | 0.038 (3) | 0.045 (3) | 0.065 (4) | −0.001 (2) | 0.007 (3) | 0.003 (3) |
Geometric parameters (Å, º) top
As1—F5 | 1.716 (4) | C14—C15 | 1.391 (8) |
As1—F4 | 1.721 (4) | C14—C19 | 1.402 (7) |
As1—F2 | 1.728 (4) | C15—C16 | 1.377 (9) |
As1—F6 | 1.734 (4) | C16—C17 | 1.370 (10) |
As1—F1 | 1.741 (3) | C17—C18 | 1.366 (11) |
As1—F3 | 1.744 (4) | C18—C19 | 1.390 (10) |
As2—F11 | 1.586 (6) | O4—C22 | 1.363 (7) |
As2—F7 | 1.620 (8) | O4—C38 | 1.373 (7) |
As2—F12 | 1.622 (6) | O5—C26 | 1.379 (8) |
As2—F9 | 1.646 (7) | O5—C28 | 1.375 (7) |
As2—F8 | 1.699 (4) | O6—C32 | 1.383 (6) |
As2—F10 | 1.695 (5) | O6—C34 | 1.391 (6) |
O1—C19 | 1.357 (8) | C20—C33 | 1.384 (7) |
O1—C3 | 1.365 (9) | C20—C27 | 1.409 (7) |
O2—C9 | 1.367 (7) | C20—C21 | 1.401 (7) |
O2—C7 | 1.381 (8) | C21—C22 | 1.400 (8) |
O3—C15 | 1.380 (7) | C21—C26 | 1.402 (8) |
O3—C13 | 1.378 (6) | C22—C23 | 1.378 (9) |
C1—C2 | 1.399 (8) | C23—C24 | 1.381 (11) |
C1—C14 | 1.386 (8) | C24—C25 | 1.379 (12) |
C1—C8 | 1.391 (7) | C25—C26 | 1.384 (9) |
C2—C7 | 1.385 (9) | C27—C32 | 1.399 (8) |
C2—C3 | 1.405 (9) | C27—C28 | 1.402 (8) |
C3—C4 | 1.399 (11) | C28—C29 | 1.380 (9) |
C4—C5 | 1.381 (14) | C29—C30 | 1.376 (10) |
C5—C6 | 1.399 (13) | C30—C31 | 1.381 (9) |
C6—C7 | 1.387 (10) | C31—C32 | 1.381 (8) |
C8—C9 | 1.402 (8) | C33—C38 | 1.408 (7) |
C8—C13 | 1.403 (7) | C33—C34 | 1.393 (8) |
C9—C10 | 1.387 (9) | C34—C35 | 1.365 (8) |
C10—C11 | 1.364 (10) | C35—C36 | 1.377 (9) |
C11—C12 | 1.397 (9) | C36—C37 | 1.380 (10) |
C12—C13 | 1.368 (8) | C37—C38 | 1.380 (8) |
| | | |
F5—As1—F4 | 88.7 (2) | O3—C13—C12 | 120.0 (5) |
F5—As1—F2 | 88.9 (2) | O3—C13—C8 | 119.9 (5) |
F4—As1—F2 | 89.0 (2) | C12—C13—C8 | 120.1 (5) |
F5—As1—F6 | 177.9 (2) | C1—C14—C15 | 119.9 (5) |
F4—As1—F6 | 89.3 (2) | C1—C14—C19 | 119.5 (6) |
F2—As1—F6 | 91.3 (2) | C15—C14—C19 | 120.6 (6) |
F5—As1—F1 | 90.1 (2) | C16—C15—O3 | 119.4 (6) |
F4—As1—F1 | 88.2 (2) | C16—C15—C14 | 120.7 (6) |
F2—As1—F1 | 177.1 (2) | O3—C15—C14 | 119.9 (5) |
F6—As1—F1 | 89.6 (2) | C15—C16—C17 | 117.1 (7) |
F5—As1—F3 | 88.9 (2) | C18—C17—C16 | 124.7 (7) |
F4—As1—F3 | 177.3 (2) | C17—C18—C19 | 118.3 (6) |
F2—As1—F3 | 92.3 (2) | O1—C19—C18 | 120.5 (6) |
F6—As1—F3 | 93.1 (2) | O1—C19—C14 | 120.8 (6) |
F1—As1—F3 | 90.4 (2) | C18—C19—C14 | 118.7 (6) |
F11—As2—F7 | 178.7 (6) | C22—O4—C38 | 120.6 (4) |
F11—As2—F12 | 95.1 (6) | C26—O5—C28 | 121.1 (5) |
F7—As2—F12 | 85.6 (6) | C32—O6—C34 | 120.1 (4) |
F11—As2—F9 | 84.0 (6) | C33—C20—C27 | 120.0 (5) |
F7—As2—F9 | 95.3 (7) | C33—C20—C21 | 120.3 (5) |
F12—As2—F9 | 179.1 (6) | C27—C20—C21 | 119.7 (5) |
F11—As2—F8 | 93.7 (5) | C22—C21—C26 | 121.8 (5) |
F7—As2—F8 | 87.4 (4) | C22—C21—C20 | 118.8 (5) |
F12—As2—F8 | 90.7 (3) | C26—C21—C20 | 119.3 (5) |
F9—As2—F8 | 89.1 (3) | O4—C22—C23 | 120.5 (6) |
F11—As2—F10 | 87.4 (5) | O4—C22—C21 | 120.8 (5) |
F7—As2—F10 | 91.5 (4) | C23—C22—C21 | 118.7 (6) |
F12—As2—F10 | 87.5 (3) | C22—C23—C24 | 118.7 (7) |
F9—As2—F10 | 92.7 (4) | C25—C24—C23 | 123.7 (7) |
F8—As2—F10 | 178.0 (3) | C24—C25—C26 | 118.1 (7) |
C19—O1—C3 | 120.1 (5) | O5—C26—C25 | 120.8 (6) |
C9—O2—C7 | 119.7 (5) | O5—C26—C21 | 120.2 (5) |
C15—O3—C13 | 120.7 (4) | C25—C26—C21 | 119.0 (7) |
C2—C1—C14 | 120.0 (5) | C32—C27—C28 | 121.4 (5) |
C2—C1—C8 | 119.7 (5) | C32—C27—C20 | 119.0 (5) |
C14—C1—C8 | 120.3 (5) | C28—C27—C20 | 119.6 (5) |
C7—C2—C1 | 118.9 (6) | C29—C28—O5 | 121.3 (6) |
C7—C2—C3 | 122.7 (6) | C29—C28—C27 | 118.9 (6) |
C1—C2—C3 | 118.4 (6) | O5—C28—C27 | 119.8 (5) |
O1—C3—C4 | 121.1 (8) | C30—C29—C28 | 118.8 (6) |
O1—C3—C2 | 121.3 (6) | C31—C30—C29 | 123.4 (6) |
C4—C3—C2 | 117.6 (8) | C30—C31—C32 | 118.4 (6) |
C5—C4—C3 | 118.5 (8) | O6—C32—C31 | 120.2 (5) |
C4—C5—C6 | 124.3 (8) | O6—C32—C27 | 120.6 (5) |
C5—C6—C7 | 116.8 (8) | C31—C32—C27 | 119.2 (5) |
C2—C7—O2 | 121.6 (5) | C20—C33—C38 | 119.3 (5) |
C2—C7—C6 | 120.0 (7) | C20—C33—C34 | 120.4 (5) |
O2—C7—C6 | 118.4 (7) | C38—C33—C34 | 120.2 (5) |
C9—C8—C1 | 119.9 (5) | C35—C34—O6 | 119.8 (5) |
C9—C8—C13 | 120.8 (5) | C35—C34—C33 | 120.3 (5) |
C1—C8—C13 | 119.2 (5) | O6—C34—C33 | 119.9 (5) |
O2—C9—C10 | 121.0 (6) | C34—C35—C36 | 118.4 (6) |
O2—C9—C8 | 120.2 (5) | C37—C36—C35 | 123.4 (6) |
C10—C9—C8 | 118.8 (6) | C38—C37—C36 | 118.2 (6) |
C11—C10—C9 | 118.9 (6) | C37—C38—O4 | 120.6 (5) |
C10—C11—C12 | 123.5 (6) | C37—C38—C33 | 119.4 (6) |
C13—C12—C11 | 117.9 (6) | O4—C38—C33 | 120.1 (5) |
(6120K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.757 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.26 mm−1 |
a = 12.946 (2) Å | T = 120 K |
c = 16.806 (3) Å | Prism, orange |
V = 2439.4 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 474 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 26.3°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8019 measured reflections | k = −16→16 |
557 independent reflections | l = −20→20 |
Refinement top
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
557 reflections | (Δ/σ)max = −0.002 |
47 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0213 (3) | |
F1 | 0.04986 (8) | 0.11667 (8) | 0.05520 (5) | 0.0319 (3) | |
O1 | 0.78471 (10) | 0.0000 | 0.2500 | 0.0267 (4) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0202 (7) | |
C2 | 1.0000 | 0.10771 (15) | 0.2500 | 0.0221 (4) | |
C3 | 0.89117 (12) | 0.10668 (12) | 0.25162 (7) | 0.0241 (4) | |
C4 | 0.89034 (14) | 0.21302 (14) | 0.25388 (8) | 0.0299 (4) | |
H4 | 0.8193 | 0.2142 | 0.2578 | 0.036* | |
C5 | 1.0000 | 0.3184 (2) | 0.2500 | 0.0322 (5) | |
H5 | 1.0000 | 0.3903 | 0.2500 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0200 (3) | 0.0200 (3) | 0.0239 (4) | 0.0100 (2) | 0.000 | 0.000 |
F1 | 0.0322 (5) | 0.0258 (5) | 0.0363 (5) | 0.0134 (4) | −0.0033 (4) | −0.0081 (4) |
O1 | 0.0231 (5) | 0.0318 (8) | 0.0280 (7) | 0.0159 (4) | 0.0008 (3) | 0.0016 (6) |
C1 | 0.0226 (10) | 0.0226 (10) | 0.0152 (14) | 0.0113 (5) | 0.000 | 0.000 |
C2 | 0.0262 (10) | 0.0245 (8) | 0.0161 (8) | 0.0131 (5) | 0.0010 (7) | 0.0005 (4) |
C3 | 0.0280 (8) | 0.0272 (8) | 0.0190 (6) | 0.0153 (7) | 0.0005 (5) | 0.0006 (5) |
C4 | 0.0401 (9) | 0.0371 (9) | 0.0233 (7) | 0.0273 (8) | −0.0028 (6) | −0.0022 (6) |
C5 | 0.0528 (14) | 0.0280 (7) | 0.0239 (9) | 0.0264 (7) | −0.0052 (9) | −0.0026 (5) |
Geometric parameters (Å, º) top
P1—F1i | 1.6074 (8) | C1—C2vii | 1.394 (2) |
P1—F1 | 1.6074 (8) | C1—C2viii | 1.394 (2) |
P1—F1ii | 1.6074 (8) | C1—C2 | 1.394 (2) |
P1—F1iii | 1.6074 (8) | C2—C3ix | 1.403 (2) |
P1—F1iv | 1.6074 (8) | C2—C3 | 1.403 (2) |
P1—F1v | 1.6074 (8) | C3—C4 | 1.383 (2) |
O1—C3 | 1.380 (2) | C4—C5 | 1.395 (2) |
O1—C3vi | 1.380 (2) | C5—C4ix | 1.395 (2) |
| | | |
F1i—P1—F1 | 180.0 | F1iv—P1—F1v | 90.02 (5) |
F1i—P1—F1ii | 89.98 (5) | C3—O1—C3vi | 120.22 (15) |
F1—P1—F1ii | 90.02 (5) | C2vii—C1—C2viii | 120.0 |
F1i—P1—F1iii | 89.98 (5) | C2vii—C1—C2 | 120.0 |
F1—P1—F1iii | 90.02 (5) | C2viii—C1—C2 | 120.0 |
F1ii—P1—F1iii | 90.02 (5) | C1—C2—C3ix | 119.52 (9) |
F1i—P1—F1iv | 90.02 (5) | C1—C2—C3 | 119.52 (9) |
F1—P1—F1iv | 89.98 (5) | C3ix—C2—C3 | 121.0 (2) |
F1ii—P1—F1iv | 89.98 (5) | O1—C3—C4 | 119.74 (13) |
F1iii—P1—F1iv | 180.0 | O1—C3—C2 | 120.33 (13) |
F1i—P1—F1v | 90.02 (5) | C4—C3—C2 | 119.93 (15) |
F1—P1—F1v | 89.98 (5) | C3—C4—C5 | 117.54 (14) |
F1ii—P1—F1v | 180.0 | C4—C5—C4ix | 124.0 (2) |
F1iii—P1—F1v | 89.98 (5) | | |
Symmetry codes: (i) −x, −y, −z; (ii) −y, x−y, z; (iii) −x+y, −x, z; (iv) x−y, x, −z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(7) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
nitratehydrogennitrate
top
Crystal data top
C19H10N2O9·HNO3·NO3 | Z = 4 |
Mr = 410.29 | F(000) = 840 |
Monoclinic, P21/n | Dx = 1.660 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4960 (13) Å | µ = 0.14 mm−1 |
b = 7.6530 (15) Å | T = 120 K |
c = 33.039 (7) Å | Plate, orange |
β = 91.95 (3)° | 0.43 × 0.18 × 0.05 mm |
V = 1641.5 (6) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 3345 independent reflections |
Radiation source: fine-focus sealed tube | 2173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.3°, θmin = 1.2° |
ω scan, frame data integration | h = −8→8 |
Absorption correction: empirical (using intensity measurements) | k = −9→9 |
Tmin = 0.776, Tmax = 0.980 | l = −41→41 |
17025 measured reflections | |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Calculated w = 1/[σ2(Fo2) + (0.0549P)2 + 0.5233P] where P = (Fo2 + 2Fc2)/3 |
3345 reflections | (Δ/σ)max = 0.002 |
271 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.7353 (2) | 0.89044 (19) | 0.16804 (4) | 0.0197 (4) | |
O2 | 0.2733 (2) | 1.00261 (19) | 0.05309 (4) | 0.0209 (4) | |
O3 | 0.1106 (2) | 1.22049 (19) | 0.18556 (4) | 0.0216 (4) | |
C1 | 0.3724 (3) | 1.0371 (3) | 0.13560 (6) | 0.0163 (5) | |
C2 | 0.5040 (3) | 0.9468 (3) | 0.11042 (6) | 0.0164 (5) | |
C3 | 0.6851 (3) | 0.8702 (3) | 0.12728 (6) | 0.0175 (5) | |
C4 | 0.8125 (3) | 0.7748 (3) | 0.10320 (7) | 0.0213 (5) | |
H4 | 0.9314 | 0.7223 | 0.1139 | 0.026* | |
C5 | 0.7569 (4) | 0.7596 (3) | 0.06216 (7) | 0.0237 (5) | |
H5 | 0.8422 | 0.6953 | 0.0457 | 0.028* | |
C6 | 0.5798 (4) | 0.8359 (3) | 0.04435 (7) | 0.0224 (5) | |
H6 | 0.5492 | 0.8244 | 0.0168 | 0.027* | |
C7 | 0.4524 (3) | 0.9288 (3) | 0.06910 (6) | 0.0179 (5) | |
C8 | 0.1912 (3) | 1.1098 (3) | 0.11928 (6) | 0.0182 (5) | |
C9 | 0.1438 (3) | 1.0947 (3) | 0.07770 (6) | 0.0192 (5) | |
C10 | −0.0301 (3) | 1.1744 (3) | 0.06117 (7) | 0.0235 (5) | |
H10 | −0.0631 | 1.1666 | 0.0336 | 0.028* | |
C11 | −0.1544 (4) | 1.2668 (3) | 0.08711 (7) | 0.0251 (5) | |
H11 | −0.2718 | 1.3205 | 0.0761 | 0.030* | |
C12 | −0.1141 (3) | 1.2843 (3) | 0.12880 (7) | 0.0242 (5) | |
H12 | −0.2017 | 1.3470 | 0.1451 | 0.029* | |
C13 | 0.0611 (3) | 1.2045 (3) | 0.14470 (6) | 0.0192 (5) | |
C14 | 0.4229 (3) | 1.0553 (3) | 0.17675 (6) | 0.0171 (5) | |
C15 | 0.2893 (3) | 1.1470 (3) | 0.20178 (6) | 0.0193 (5) | |
C16 | 0.3357 (4) | 1.1634 (3) | 0.24261 (7) | 0.0246 (5) | |
H16 | 0.2479 | 1.2217 | 0.2597 | 0.029* | |
C17 | 0.5194 (4) | 1.0892 (3) | 0.25738 (7) | 0.0247 (5) | |
H17 | 0.5523 | 1.1006 | 0.2849 | 0.030* | |
C18 | 0.6572 (4) | 0.9988 (3) | 0.23348 (7) | 0.0231 (5) | |
H18 | 0.7785 | 0.9521 | 0.2446 | 0.028* | |
C19 | 0.6070 (3) | 0.9813 (3) | 0.19297 (7) | 0.0188 (5) | |
N1 | 0.2727 (3) | 0.5112 (2) | 0.03952 (6) | 0.0213 (4) | |
O4 | 0.2160 (2) | 0.58203 (19) | 0.07456 (4) | 0.0230 (4) | |
H4A | 0.2701 | 0.5281 | 0.0935 | 0.035* | 0.50 |
O5 | 0.3911 (2) | 0.3865 (2) | 0.04094 (5) | 0.0268 (4) | |
O6 | 0.1997 (3) | 0.5790 (2) | 0.00891 (5) | 0.0307 (4) | |
N2 | 0.4074 (3) | 0.5514 (2) | 0.16270 (6) | 0.0216 (4) | |
O7 | 0.2678 (3) | 0.6628 (2) | 0.16200 (5) | 0.0276 (4) | |
O8 | 0.5267 (3) | 0.5279 (2) | 0.19189 (5) | 0.0353 (5) | |
O9 | 0.4293 (2) | 0.45440 (19) | 0.13082 (5) | 0.0250 (4) | |
H9 | 0.3957 | 0.3537 | 0.1359 | 0.038* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0199 (8) | 0.0211 (8) | 0.0180 (8) | 0.0043 (6) | 0.0003 (6) | −0.0006 (6) |
O2 | 0.0225 (9) | 0.0213 (8) | 0.0187 (8) | −0.0001 (7) | −0.0024 (7) | −0.0001 (6) |
O3 | 0.0200 (9) | 0.0250 (8) | 0.0199 (8) | 0.0040 (7) | 0.0025 (7) | −0.0004 (6) |
C1 | 0.0178 (12) | 0.0124 (10) | 0.0189 (12) | −0.0039 (8) | 0.0020 (9) | 0.0021 (8) |
C2 | 0.0167 (11) | 0.0145 (11) | 0.0179 (11) | −0.0025 (8) | 0.0002 (9) | −0.0003 (8) |
C3 | 0.0196 (12) | 0.0169 (11) | 0.0162 (11) | −0.0025 (9) | 0.0014 (9) | 0.0015 (9) |
C4 | 0.0214 (13) | 0.0174 (11) | 0.0251 (13) | 0.0012 (9) | 0.0019 (10) | −0.0009 (9) |
C5 | 0.0234 (13) | 0.0187 (11) | 0.0295 (14) | −0.0008 (9) | 0.0086 (10) | −0.0040 (10) |
C6 | 0.0275 (13) | 0.0211 (12) | 0.0188 (12) | −0.0046 (10) | 0.0034 (10) | −0.0018 (9) |
C7 | 0.0166 (12) | 0.0161 (11) | 0.0208 (12) | −0.0039 (9) | −0.0011 (9) | 0.0014 (9) |
C8 | 0.0168 (11) | 0.0174 (11) | 0.0204 (12) | −0.0030 (9) | 0.0000 (9) | 0.0030 (9) |
C9 | 0.0185 (12) | 0.0169 (11) | 0.0223 (12) | −0.0045 (9) | 0.0005 (9) | 0.0012 (9) |
C10 | 0.0239 (13) | 0.0227 (12) | 0.0234 (12) | −0.0055 (10) | −0.0054 (10) | 0.0041 (10) |
C11 | 0.0179 (12) | 0.0236 (13) | 0.0335 (14) | −0.0015 (9) | −0.0045 (11) | 0.0062 (10) |
C12 | 0.0176 (12) | 0.0203 (12) | 0.0350 (14) | 0.0004 (9) | 0.0047 (10) | 0.0031 (10) |
C13 | 0.0182 (12) | 0.0166 (11) | 0.0230 (12) | −0.0031 (9) | 0.0008 (10) | 0.0019 (9) |
C14 | 0.0183 (12) | 0.0168 (11) | 0.0164 (11) | −0.0032 (9) | 0.0016 (9) | 0.0014 (9) |
C15 | 0.0203 (12) | 0.0175 (11) | 0.0202 (12) | −0.0009 (9) | 0.0013 (9) | 0.0011 (9) |
C16 | 0.0318 (14) | 0.0214 (12) | 0.0209 (12) | −0.0021 (10) | 0.0073 (10) | −0.0018 (9) |
C17 | 0.0335 (14) | 0.0248 (12) | 0.0155 (11) | −0.0041 (11) | −0.0008 (10) | 0.0004 (9) |
C18 | 0.0267 (13) | 0.0216 (11) | 0.0208 (12) | 0.0014 (10) | −0.0038 (10) | 0.0010 (9) |
C19 | 0.0201 (12) | 0.0161 (11) | 0.0201 (12) | −0.0006 (9) | 0.0018 (9) | 0.0009 (9) |
N1 | 0.0176 (10) | 0.0249 (10) | 0.0216 (11) | −0.0039 (8) | 0.0021 (8) | −0.0031 (8) |
O4 | 0.0242 (9) | 0.0267 (8) | 0.0182 (8) | 0.0056 (7) | 0.0016 (7) | −0.0032 (7) |
O5 | 0.0262 (9) | 0.0242 (9) | 0.0301 (10) | 0.0060 (7) | 0.0033 (7) | −0.0055 (7) |
O6 | 0.0326 (10) | 0.0381 (10) | 0.0212 (9) | 0.0016 (8) | −0.0048 (8) | 0.0039 (7) |
N2 | 0.0245 (11) | 0.0205 (10) | 0.0199 (10) | −0.0056 (8) | 0.0022 (9) | 0.0019 (8) |
O7 | 0.0365 (10) | 0.0242 (9) | 0.0223 (9) | 0.0066 (8) | 0.0045 (7) | 0.0002 (7) |
O8 | 0.0343 (11) | 0.0475 (11) | 0.0234 (10) | −0.0017 (8) | −0.0106 (8) | 0.0009 (8) |
O9 | 0.0270 (9) | 0.0231 (8) | 0.0248 (9) | 0.0017 (7) | −0.0013 (7) | −0.0040 (7) |
Geometric parameters (Å, º) top
O1—C19 | 1.380 (3) | C9—C10 | 1.381 (3) |
O1—C3 | 1.383 (2) | C10—C11 | 1.390 (3) |
O2—C9 | 1.382 (3) | C11—C12 | 1.400 (3) |
O2—C7 | 1.382 (3) | C12—C13 | 1.379 (3) |
O3—C15 | 1.381 (3) | C14—C15 | 1.407 (3) |
O3—C13 | 1.382 (3) | C14—C19 | 1.412 (3) |
C1—C8 | 1.394 (3) | C15—C16 | 1.378 (3) |
C1—C14 | 1.395 (3) | C16—C17 | 1.395 (3) |
C1—C2 | 1.396 (3) | C17—C18 | 1.397 (3) |
C2—C7 | 1.401 (3) | C18—C19 | 1.373 (3) |
C2—C3 | 1.412 (3) | N1—O6 | 1.218 (2) |
C3—C4 | 1.376 (3) | N1—O5 | 1.226 (2) |
C4—C5 | 1.396 (3) | N1—O4 | 1.341 (2) |
C5—C6 | 1.402 (3) | N2—O8 | 1.230 (2) |
C6—C7 | 1.380 (3) | N2—O7 | 1.244 (2) |
C8—C9 | 1.402 (3) | N2—O9 | 1.300 (2) |
C8—C13 | 1.412 (3) | | |
| | | |
C19—O1—C3 | 120.69 (16) | C9—C10—C11 | 117.8 (2) |
C9—O2—C7 | 120.29 (16) | C10—C11—C12 | 124.2 (2) |
C15—O3—C13 | 120.49 (17) | C13—C12—C11 | 117.2 (2) |
C8—C1—C14 | 120.3 (2) | C12—C13—O3 | 119.6 (2) |
C8—C1—C2 | 119.56 (19) | C12—C13—C8 | 120.2 (2) |
C14—C1—C2 | 120.11 (19) | O3—C13—C8 | 120.15 (19) |
C1—C2—C7 | 119.88 (19) | C1—C14—C15 | 119.6 (2) |
C1—C2—C3 | 119.30 (19) | C1—C14—C19 | 119.9 (2) |
C7—C2—C3 | 120.80 (19) | C15—C14—C19 | 120.56 (19) |
C4—C3—O1 | 119.71 (19) | C16—C15—O3 | 119.7 (2) |
C4—C3—C2 | 120.08 (19) | C16—C15—C14 | 120.1 (2) |
O1—C3—C2 | 120.21 (18) | O3—C15—C14 | 120.15 (19) |
C3—C4—C5 | 117.7 (2) | C15—C16—C17 | 117.5 (2) |
C4—C5—C6 | 123.7 (2) | C16—C17—C18 | 124.1 (2) |
C7—C6—C5 | 117.8 (2) | C19—C18—C17 | 117.6 (2) |
C6—C7—O2 | 119.86 (19) | C18—C19—O1 | 120.18 (19) |
C6—C7—C2 | 120.0 (2) | C18—C19—C14 | 120.0 (2) |
O2—C7—C2 | 120.18 (19) | O1—C19—C14 | 119.77 (18) |
C1—C8—C9 | 120.0 (2) | O6—N1—O5 | 126.13 (19) |
C1—C8—C13 | 119.30 (19) | O6—N1—O4 | 115.70 (18) |
C9—C8—C13 | 120.6 (2) | O5—N1—O4 | 118.17 (18) |
C10—C9—O2 | 119.94 (19) | O8—N2—O7 | 123.66 (19) |
C10—C9—C8 | 120.0 (2) | O8—N2—O9 | 117.93 (19) |
O2—C9—C8 | 120.05 (19) | O7—N2—O9 | 118.41 (18) |
(8) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
trifluoromethanesulphonate
top
Crystal data top
C19H9O3·CF3O3S | Z = 8 |
Mr = 434.33 | F(000) = 1760 |
Monoclinic, P21/c | Dx = 1.711 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.771 (3) Å | µ = 0.27 mm−1 |
b = 15.473 (3) Å | T = 120 K |
c = 15.332 (3) Å | Plate, orange |
β = 115.70 (3)° | 0.45 × 0.30 × 0.23 mm |
V = 3371.3 (12) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 6860 independent reflections |
Radiation source: fine-focus sealed tube | 5770 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scan, frame data integration | θmax = 26.3°, θmin = 1.4° |
Absorption correction: empirical (using intensity measurements) | h = −19→19 |
Tmin = 0.776, Tmax = 0.980 | k = −19→19 |
35210 measured reflections | l = −19→19 |
Refinement top
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Calculated w = 1/[σ2(Fo2) + (0.0524P)2 + 1.1788P] where P = (Fo2 + 2Fc2)/3 |
6860 reflections | (Δ/σ)max = −0.002 |
541 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.04323 (2) | 0.33597 (2) | 0.34450 (2) | 0.01593 (9) | |
F1 | 0.03354 (7) | 0.39911 (7) | 0.49895 (7) | 0.0348 (2) | |
F2 | 0.17308 (6) | 0.40083 (7) | 0.50603 (7) | 0.0335 (2) | |
F3 | 0.06916 (7) | 0.49326 (6) | 0.41656 (7) | 0.0345 (2) | |
O7 | 0.09944 (7) | 0.36086 (7) | 0.29540 (8) | 0.0228 (2) | |
O8 | 0.06597 (8) | 0.25271 (7) | 0.39159 (8) | 0.0268 (3) | |
O9 | −0.05613 (7) | 0.35477 (7) | 0.29248 (8) | 0.0241 (2) | |
C39 | 0.08176 (11) | 0.41085 (10) | 0.44655 (11) | 0.0219 (3) | |
S2 | 0.49800 (3) | 0.62201 (2) | 0.21757 (3) | 0.02098 (10) | |
F4 | 0.35412 (7) | 0.53216 (7) | 0.09460 (7) | 0.0329 (2) | |
F5 | 0.38414 (8) | 0.64883 (8) | 0.03540 (8) | 0.0444 (3) | |
F6 | 0.47308 (9) | 0.53659 (9) | 0.06091 (10) | 0.0561 (4) | |
O10 | 0.56353 (8) | 0.67735 (7) | 0.20111 (9) | 0.0305 (3) | |
O11 | 0.43225 (9) | 0.66602 (7) | 0.24429 (9) | 0.0296 (3) | |
O12 | 0.53778 (10) | 0.54445 (8) | 0.27151 (10) | 0.0451 (4) | |
C40 | 0.42377 (12) | 0.58286 (11) | 0.09589 (12) | 0.0272 (4) | |
O1 | 0.02209 (7) | 0.67067 (7) | 0.30620 (7) | 0.0199 (2) | |
O2 | 0.11471 (7) | 0.46579 (7) | 0.12605 (7) | 0.0216 (2) | |
O3 | −0.19868 (7) | 0.45498 (7) | 0.10766 (7) | 0.0213 (2) | |
C1 | −0.02069 (10) | 0.53023 (9) | 0.18029 (10) | 0.0172 (3) | |
C2 | 0.06860 (10) | 0.56772 (9) | 0.21666 (10) | 0.0175 (3) | |
C3 | 0.08880 (10) | 0.63931 (10) | 0.27893 (10) | 0.0190 (3) | |
C4 | 0.17619 (11) | 0.67793 (10) | 0.31357 (11) | 0.0233 (3) | |
H4 | 0.1906 | 0.7257 | 0.3544 | 0.028* | |
C5 | 0.24243 (11) | 0.64320 (11) | 0.28554 (12) | 0.0246 (3) | |
H5 | 0.3014 | 0.6691 | 0.3088 | 0.029* | |
C6 | 0.22497 (11) | 0.57175 (10) | 0.22458 (11) | 0.0231 (3) | |
H6 | 0.2711 | 0.5501 | 0.2081 | 0.028* | |
C7 | 0.13662 (10) | 0.53421 (10) | 0.18951 (10) | 0.0196 (3) | |
C8 | −0.04223 (10) | 0.46058 (10) | 0.11644 (10) | 0.0187 (3) | |
C9 | 0.02676 (10) | 0.42856 (10) | 0.08996 (10) | 0.0201 (3) | |
C10 | 0.00572 (12) | 0.36032 (10) | 0.02617 (11) | 0.0246 (3) | |
H10 | 0.0501 | 0.3388 | 0.0071 | 0.030* | |
C11 | −0.08413 (12) | 0.32448 (10) | −0.00885 (11) | 0.0266 (3) | |
H11 | −0.0984 | 0.2783 | −0.0517 | 0.032* | |
C12 | −0.15383 (12) | 0.35412 (10) | 0.01690 (11) | 0.0246 (3) | |
H12 | −0.2129 | 0.3284 | −0.0079 | 0.030* | |
C13 | −0.13211 (11) | 0.42298 (10) | 0.08041 (10) | 0.0202 (3) | |
C14 | −0.08840 (10) | 0.56311 (9) | 0.20675 (10) | 0.0176 (3) | |
C15 | −0.17839 (10) | 0.52483 (10) | 0.16944 (10) | 0.0188 (3) | |
C16 | −0.24617 (10) | 0.55783 (10) | 0.19418 (11) | 0.0225 (3) | |
H16 | −0.3058 | 0.5333 | 0.1706 | 0.027* | |
C17 | −0.22245 (11) | 0.62949 (11) | 0.25597 (11) | 0.0238 (3) | |
H17 | −0.2680 | 0.6519 | 0.2729 | 0.029* | |
C18 | −0.13430 (11) | 0.66912 (10) | 0.29347 (11) | 0.0220 (3) | |
H18 | −0.1215 | 0.7172 | 0.3336 | 0.026* | |
C19 | −0.06671 (10) | 0.63469 (10) | 0.26903 (10) | 0.0188 (3) | |
O4 | 0.43422 (8) | 0.66177 (7) | 0.85196 (8) | 0.0238 (2) | |
O5 | 0.38058 (7) | 0.60993 (7) | 0.52163 (8) | 0.0225 (2) | |
O6 | 0.69698 (7) | 0.64935 (7) | 0.76972 (8) | 0.0239 (2) | |
C20 | 0.50397 (10) | 0.64049 (9) | 0.71449 (11) | 0.0178 (3) | |
C21 | 0.40731 (10) | 0.63707 (9) | 0.68652 (11) | 0.0185 (3) | |
C22 | 0.37310 (11) | 0.64680 (9) | 0.75670 (11) | 0.0208 (3) | |
C23 | 0.27765 (12) | 0.64035 (10) | 0.73010 (13) | 0.0253 (3) | |
H23 | 0.2537 | 0.6472 | 0.7754 | 0.030* | |
C24 | 0.21844 (11) | 0.62332 (10) | 0.63327 (13) | 0.0275 (4) | |
H24 | 0.1542 | 0.6183 | 0.6152 | 0.033* | |
C25 | 0.25048 (11) | 0.61347 (10) | 0.56201 (12) | 0.0256 (3) | |
H25 | 0.2088 | 0.6026 | 0.4980 | 0.031* | |
C26 | 0.34606 (11) | 0.62040 (10) | 0.58955 (11) | 0.0207 (3) | |
C27 | 0.53878 (10) | 0.62865 (9) | 0.64590 (11) | 0.0187 (3) | |
C28 | 0.47626 (10) | 0.61349 (9) | 0.54864 (11) | 0.0199 (3) | |
C29 | 0.51029 (11) | 0.60131 (10) | 0.48059 (11) | 0.0238 (3) | |
H29 | 0.4697 | 0.5924 | 0.4158 | 0.029* | |
C30 | 0.60761 (11) | 0.60275 (11) | 0.51190 (12) | 0.0260 (3) | |
H30 | 0.6309 | 0.5933 | 0.4664 | 0.031* | |
C31 | 0.67215 (11) | 0.61756 (11) | 0.60794 (12) | 0.0252 (3) | |
H31 | 0.7366 | 0.6177 | 0.6262 | 0.030* | |
C32 | 0.63655 (10) | 0.63202 (10) | 0.67468 (11) | 0.0209 (3) | |
C33 | 0.56568 (11) | 0.65564 (9) | 0.81097 (11) | 0.0198 (3) | |
C34 | 0.66265 (11) | 0.66184 (10) | 0.83758 (11) | 0.0228 (3) | |
C35 | 0.72378 (12) | 0.68139 (11) | 0.93177 (12) | 0.0285 (4) | |
H35 | 0.7880 | 0.6873 | 0.9504 | 0.034* | |
C36 | 0.68603 (13) | 0.69196 (11) | 0.99826 (12) | 0.0301 (4) | |
H36 | 0.7271 | 0.7048 | 1.0620 | 0.036* | |
C37 | 0.59048 (13) | 0.68442 (11) | 0.97491 (12) | 0.0282 (4) | |
H37 | 0.5684 | 0.6907 | 1.0218 | 0.034* | |
C38 | 0.52968 (11) | 0.66725 (10) | 0.87962 (11) | 0.0225 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0154 (2) | 0.0183 (2) | 0.0140 (2) | −0.00032 (13) | 0.00631 (13) | 0.00128 (13) |
F1 | 0.0382 (6) | 0.0494 (6) | 0.0224 (5) | 0.0042 (5) | 0.0185 (4) | −0.0022 (4) |
F2 | 0.0230 (5) | 0.0436 (6) | 0.0223 (5) | −0.0008 (4) | −0.0010 (4) | −0.0053 (4) |
F3 | 0.0464 (6) | 0.0208 (5) | 0.0291 (5) | 0.0004 (4) | 0.0098 (5) | −0.0027 (4) |
O7 | 0.0194 (5) | 0.0317 (6) | 0.0197 (5) | 0.0003 (4) | 0.0109 (4) | 0.0034 (4) |
O8 | 0.0371 (7) | 0.0201 (6) | 0.0215 (6) | 0.0007 (5) | 0.0111 (5) | 0.0046 (4) |
O9 | 0.0146 (5) | 0.0345 (6) | 0.0209 (5) | −0.0014 (4) | 0.0055 (4) | −0.0004 (5) |
C39 | 0.0222 (7) | 0.0246 (8) | 0.0178 (7) | 0.0009 (6) | 0.0075 (6) | −0.0006 (6) |
S2 | 0.0209 (2) | 0.0156 (2) | 0.0246 (2) | 0.00064 (14) | 0.00815 (15) | −0.00097 (14) |
F4 | 0.0297 (5) | 0.0358 (6) | 0.0334 (5) | −0.0137 (4) | 0.0138 (4) | −0.0075 (4) |
F5 | 0.0441 (6) | 0.0567 (7) | 0.0248 (5) | −0.0139 (5) | 0.0078 (5) | 0.0094 (5) |
F6 | 0.0645 (8) | 0.0584 (8) | 0.0717 (8) | −0.0213 (6) | 0.0543 (7) | −0.0395 (7) |
O10 | 0.0229 (6) | 0.0243 (6) | 0.0466 (7) | −0.0048 (5) | 0.0172 (5) | −0.0070 (5) |
O11 | 0.0375 (7) | 0.0266 (6) | 0.0350 (7) | −0.0030 (5) | 0.0254 (6) | −0.0062 (5) |
O12 | 0.0442 (8) | 0.0236 (6) | 0.0490 (8) | 0.0052 (6) | 0.0028 (7) | 0.0089 (6) |
C40 | 0.0287 (8) | 0.0306 (9) | 0.0282 (8) | −0.0064 (7) | 0.0181 (7) | −0.0067 (7) |
O1 | 0.0180 (5) | 0.0221 (5) | 0.0207 (5) | 0.0004 (4) | 0.0095 (4) | −0.0012 (4) |
O2 | 0.0223 (5) | 0.0238 (5) | 0.0214 (5) | 0.0047 (4) | 0.0121 (4) | 0.0016 (4) |
O3 | 0.0188 (5) | 0.0234 (5) | 0.0207 (5) | −0.0016 (4) | 0.0077 (4) | 0.0008 (4) |
C1 | 0.0198 (7) | 0.0176 (7) | 0.0136 (6) | 0.0032 (6) | 0.0066 (6) | 0.0072 (5) |
C2 | 0.0178 (7) | 0.0199 (7) | 0.0154 (7) | 0.0028 (6) | 0.0076 (6) | 0.0053 (6) |
C3 | 0.0181 (7) | 0.0215 (7) | 0.0180 (7) | 0.0039 (6) | 0.0084 (6) | 0.0052 (6) |
C4 | 0.0217 (8) | 0.0231 (8) | 0.0234 (8) | −0.0011 (6) | 0.0082 (6) | 0.0023 (6) |
C5 | 0.0159 (7) | 0.0287 (8) | 0.0277 (8) | −0.0006 (6) | 0.0082 (6) | 0.0075 (7) |
C6 | 0.0190 (7) | 0.0288 (8) | 0.0251 (8) | 0.0063 (6) | 0.0130 (6) | 0.0086 (6) |
C7 | 0.0215 (7) | 0.0208 (7) | 0.0174 (7) | 0.0045 (6) | 0.0094 (6) | 0.0056 (6) |
C8 | 0.0221 (7) | 0.0194 (7) | 0.0142 (7) | 0.0027 (6) | 0.0075 (6) | 0.0044 (6) |
C9 | 0.0225 (7) | 0.0219 (7) | 0.0157 (7) | 0.0045 (6) | 0.0081 (6) | 0.0064 (6) |
C10 | 0.0334 (9) | 0.0231 (8) | 0.0191 (7) | 0.0087 (7) | 0.0130 (7) | 0.0039 (6) |
C11 | 0.0386 (9) | 0.0201 (8) | 0.0194 (8) | 0.0037 (7) | 0.0109 (7) | 0.0006 (6) |
C12 | 0.0286 (8) | 0.0219 (8) | 0.0194 (7) | −0.0023 (6) | 0.0067 (6) | 0.0023 (6) |
C13 | 0.0236 (7) | 0.0207 (7) | 0.0165 (7) | 0.0027 (6) | 0.0089 (6) | 0.0052 (6) |
C14 | 0.0175 (7) | 0.0204 (7) | 0.0151 (7) | 0.0024 (6) | 0.0072 (6) | 0.0049 (6) |
C15 | 0.0200 (7) | 0.0193 (7) | 0.0158 (7) | 0.0013 (6) | 0.0064 (6) | 0.0044 (6) |
C16 | 0.0167 (7) | 0.0276 (8) | 0.0240 (8) | 0.0015 (6) | 0.0094 (6) | 0.0076 (6) |
C17 | 0.0220 (8) | 0.0285 (8) | 0.0258 (8) | 0.0074 (6) | 0.0150 (7) | 0.0077 (7) |
C18 | 0.0244 (8) | 0.0234 (8) | 0.0207 (8) | 0.0042 (6) | 0.0120 (6) | 0.0013 (6) |
C19 | 0.0179 (7) | 0.0211 (7) | 0.0170 (7) | 0.0011 (6) | 0.0072 (6) | 0.0044 (6) |
O4 | 0.0274 (6) | 0.0236 (6) | 0.0248 (6) | 0.0002 (4) | 0.0154 (5) | 0.0025 (4) |
O5 | 0.0166 (5) | 0.0279 (6) | 0.0225 (5) | −0.0024 (4) | 0.0080 (4) | −0.0025 (4) |
O6 | 0.0163 (5) | 0.0288 (6) | 0.0242 (6) | 0.0002 (4) | 0.0066 (4) | 0.0037 (5) |
C20 | 0.0192 (7) | 0.0113 (6) | 0.0227 (7) | 0.0004 (5) | 0.0089 (6) | 0.0026 (5) |
C21 | 0.0186 (7) | 0.0134 (7) | 0.0251 (8) | 0.0013 (5) | 0.0110 (6) | 0.0023 (6) |
C22 | 0.0247 (8) | 0.0132 (7) | 0.0269 (8) | 0.0012 (6) | 0.0135 (7) | 0.0031 (6) |
C23 | 0.0267 (8) | 0.0190 (7) | 0.0390 (9) | 0.0017 (6) | 0.0223 (7) | 0.0046 (7) |
C24 | 0.0192 (8) | 0.0229 (8) | 0.0435 (10) | 0.0011 (6) | 0.0165 (7) | 0.0061 (7) |
C25 | 0.0185 (7) | 0.0257 (8) | 0.0306 (8) | −0.0013 (6) | 0.0086 (6) | 0.0028 (7) |
C26 | 0.0196 (7) | 0.0176 (7) | 0.0262 (8) | 0.0003 (6) | 0.0113 (6) | 0.0013 (6) |
C27 | 0.0170 (7) | 0.0155 (7) | 0.0239 (8) | 0.0009 (5) | 0.0092 (6) | 0.0019 (6) |
C28 | 0.0163 (7) | 0.0173 (7) | 0.0255 (8) | 0.0005 (6) | 0.0085 (6) | 0.0004 (6) |
C29 | 0.0257 (8) | 0.0238 (8) | 0.0226 (8) | −0.0008 (6) | 0.0112 (6) | −0.0009 (6) |
C30 | 0.0284 (9) | 0.0253 (8) | 0.0320 (9) | 0.0023 (7) | 0.0203 (7) | 0.0019 (7) |
C31 | 0.0182 (7) | 0.0268 (8) | 0.0332 (9) | 0.0023 (6) | 0.0135 (7) | 0.0050 (7) |
C32 | 0.0180 (7) | 0.0191 (7) | 0.0237 (8) | 0.0011 (6) | 0.0075 (6) | 0.0044 (6) |
C33 | 0.0217 (8) | 0.0150 (7) | 0.0212 (7) | 0.0006 (6) | 0.0079 (6) | 0.0039 (6) |
C34 | 0.0229 (8) | 0.0197 (7) | 0.0238 (8) | 0.0010 (6) | 0.0082 (6) | 0.0055 (6) |
C35 | 0.0240 (8) | 0.0271 (8) | 0.0262 (8) | −0.0010 (7) | 0.0030 (7) | 0.0050 (7) |
C36 | 0.0374 (10) | 0.0242 (8) | 0.0194 (8) | −0.0019 (7) | 0.0038 (7) | 0.0029 (6) |
C37 | 0.0400 (10) | 0.0235 (8) | 0.0220 (8) | −0.0008 (7) | 0.0143 (7) | 0.0036 (6) |
C38 | 0.0282 (8) | 0.0163 (7) | 0.0250 (8) | 0.0006 (6) | 0.0134 (7) | 0.0046 (6) |
Geometric parameters (Å, º) top
S1—O7 | 1.4422 (11) | C12—C13 | 1.382 (2) |
S1—O8 | 1.4439 (11) | C14—C19 | 1.404 (2) |
S1—O9 | 1.4464 (12) | C14—C15 | 1.410 (2) |
S1—C39 | 1.826 (2) | C15—C16 | 1.378 (2) |
F1—C39 | 1.337 (2) | C16—C17 | 1.400 (2) |
F2—C39 | 1.338 (2) | C17—C18 | 1.395 (2) |
F3—C39 | 1.341 (2) | C18—C19 | 1.381 (2) |
S2—O12 | 1.4380 (13) | O4—C22 | 1.377 (2) |
S2—O11 | 1.4405 (12) | O4—C38 | 1.378 (2) |
S2—O10 | 1.4462 (12) | O5—C26 | 1.378 (2) |
S2—C40 | 1.823 (2) | O5—C28 | 1.382 (2) |
F4—C40 | 1.343 (2) | O6—C34 | 1.379 (2) |
F5—C40 | 1.338 (2) | O6—C32 | 1.378 (2) |
F6—C40 | 1.329 (2) | C20—C27 | 1.393 (2) |
O1—C3 | 1.378 (2) | C20—C21 | 1.394 (2) |
O1—C19 | 1.380 (2) | C20—C33 | 1.393 (2) |
O2—C9 | 1.377 (2) | C21—C26 | 1.402 (2) |
O2—C7 | 1.377 (2) | C21—C22 | 1.405 (2) |
O3—C15 | 1.380 (2) | C22—C23 | 1.382 (2) |
O3—C13 | 1.379 (2) | C23—C24 | 1.394 (3) |
C1—C14 | 1.393 (2) | C24—C25 | 1.397 (2) |
C1—C8 | 1.395 (2) | C25—C26 | 1.382 (2) |
C1—C2 | 1.396 (2) | C27—C32 | 1.409 (2) |
C2—C7 | 1.407 (2) | C27—C28 | 1.406 (2) |
C2—C3 | 1.406 (2) | C28—C29 | 1.378 (2) |
C3—C4 | 1.380 (2) | C29—C30 | 1.396 (2) |
C4—C5 | 1.398 (2) | C30—C31 | 1.399 (2) |
C5—C6 | 1.396 (2) | C31—C32 | 1.382 (2) |
C6—C7 | 1.385 (2) | C33—C34 | 1.405 (2) |
C8—C13 | 1.405 (2) | C33—C38 | 1.407 (2) |
C8—C9 | 1.406 (2) | C34—C35 | 1.378 (2) |
C9—C10 | 1.378 (2) | C35—C36 | 1.395 (3) |
C10—C11 | 1.394 (2) | C36—C37 | 1.395 (3) |
C11—C12 | 1.397 (2) | C37—C38 | 1.382 (2) |
| | | |
O7—S1—O8 | 115.06 (7) | C1—C14—C19 | 119.65 (13) |
O7—S1—O9 | 115.00 (7) | C1—C14—C15 | 119.50 (14) |
O8—S1—O9 | 115.47 (7) | C19—C14—C15 | 120.85 (13) |
O7—S1—C39 | 103.08 (7) | C16—C15—O3 | 120.17 (13) |
O8—S1—C39 | 102.68 (7) | C16—C15—C14 | 119.81 (14) |
O9—S1—C39 | 102.90 (7) | O3—C15—C14 | 120.03 (13) |
F1—C39—F2 | 107.41 (12) | C15—C16—C17 | 117.92 (14) |
F1—C39—F3 | 107.27 (13) | C18—C17—C16 | 123.59 (14) |
F2—C39—F3 | 107.43 (13) | C19—C18—C17 | 117.85 (14) |
F1—C39—S1 | 111.34 (11) | O1—C19—C18 | 119.80 (14) |
F2—C39—S1 | 111.74 (11) | O1—C19—C14 | 120.22 (13) |
F3—C39—S1 | 111.40 (10) | C18—C19—C14 | 119.98 (14) |
O12—S2—O11 | 114.79 (9) | C22—O4—C38 | 120.37 (12) |
O12—S2—O10 | 115.33 (8) | C26—O5—C28 | 120.45 (12) |
O11—S2—O10 | 115.27 (7) | C34—O6—C32 | 120.49 (12) |
O12—S2—C40 | 103.74 (8) | C27—C20—C21 | 119.93 (14) |
O11—S2—C40 | 103.07 (8) | C27—C20—C33 | 120.06 (14) |
O10—S2—C40 | 102.03 (8) | C21—C20—C33 | 120.00 (14) |
F6—C40—F5 | 108.08 (14) | C20—C21—C26 | 119.47 (14) |
F6—C40—F4 | 107.29 (14) | C20—C21—C22 | 119.47 (14) |
F5—C40—F4 | 107.59 (14) | C26—C21—C22 | 121.00 (14) |
F6—C40—S2 | 111.31 (12) | O4—C22—C23 | 119.81 (14) |
F5—C40—S2 | 110.83 (12) | O4—C22—C21 | 120.38 (14) |
F4—C40—S2 | 111.55 (11) | C23—C22—C21 | 119.81 (15) |
C3—O1—C19 | 120.29 (12) | C22—C23—C24 | 117.95 (15) |
C9—O2—C7 | 120.40 (12) | C23—C24—C25 | 123.45 (15) |
C15—O3—C13 | 120.58 (12) | C26—C25—C24 | 118.0 (2) |
C14—C1—C8 | 120.16 (14) | O5—C26—C25 | 119.74 (14) |
C14—C1—C2 | 119.99 (14) | O5—C26—C21 | 120.45 (13) |
C8—C1—C2 | 119.84 (14) | C25—C26—C21 | 119.81 (15) |
C1—C2—C7 | 119.67 (14) | C20—C27—C32 | 119.64 (14) |
C1—C2—C3 | 119.40 (13) | C20—C27—C28 | 119.85 (14) |
C7—C2—C3 | 120.93 (14) | C32—C27—C28 | 120.50 (14) |
C4—C3—O1 | 119.82 (14) | C29—C28—O5 | 120.07 (14) |
C4—C3—C2 | 119.80 (14) | C29—C28—C27 | 120.12 (14) |
O1—C3—C2 | 120.37 (13) | O5—C28—C27 | 119.81 (14) |
C3—C4—C5 | 118.04 (15) | C28—C29—C30 | 117.96 (14) |
C6—C5—C4 | 123.61 (14) | C29—C30—C31 | 123.66 (15) |
C7—C6—C5 | 117.73 (14) | C32—C31—C30 | 117.52 (14) |
O2—C7—C6 | 119.92 (13) | C31—C32—O6 | 119.85 (14) |
O2—C7—C2 | 120.17 (13) | C31—C32—C27 | 120.19 (14) |
C6—C7—C2 | 119.88 (14) | O6—C32—C27 | 119.97 (14) |
C1—C8—C13 | 119.53 (14) | C20—C33—C34 | 119.41 (15) |
C1—C8—C9 | 119.42 (14) | C20—C33—C38 | 119.53 (14) |
C13—C8—C9 | 121.04 (14) | C34—C33—C38 | 121.03 (14) |
O2—C9—C10 | 119.74 (14) | O6—C34—C35 | 119.76 (14) |
O2—C9—C8 | 120.49 (13) | O6—C34—C33 | 120.36 (14) |
C10—C9—C8 | 119.76 (14) | C35—C34—C33 | 119.9 (2) |
C9—C10—C11 | 118.00 (15) | C34—C35—C36 | 117.7 (2) |
C10—C11—C12 | 123.62 (15) | C37—C36—C35 | 124.0 (2) |
C13—C12—C11 | 117.85 (15) | C38—C37—C36 | 117.7 (2) |
C12—C13—O3 | 120.09 (14) | O4—C38—C37 | 120.10 (15) |
C12—C13—C8 | 119.72 (14) | O4—C38—C33 | 120.20 (14) |
O3—C13—C8 | 120.19 (13) | C37—C38—C33 | 119.7 (2) |
(9) Bis(4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium)
tetradecachlorohexamolybdate
top
Crystal data top
C19H9O3·Cl7Mo3 | Z = 8 |
Mr = 821.23 | F(000) = 3136 |
Monoclinic, C2/c | Dx = 2.392 Mg m−3 |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.205 (4) Å | µ = 2.47 mm−1 |
b = 13.540 (3) Å | T = 120 K |
c = 18.679 (4) Å | Prism, orange |
β = 97.93 (3)° | 0.18 × 0.13 × 0.10 mm |
V = 4560.3 (16) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 4631 independent reflections |
Radiation source: fine-focus sealed tube | 4029 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scan, frame data integration | θmax = 26.3°, θmin = 1.9° |
Absorption correction: empirical (using intensity measurements) | h = −22→22 |
Tmin = 0.776, Tmax = 0.862 | k = −16→16 |
23431 measured reflections | l = −23→23 |
Refinement top
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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Calculated w = 1/[σ2(Fo2) + (0.031P)2 + 4.5834P] where P = (Fo2 + 2Fc2)/3 |
4631 reflections | (Δ/σ)max = 0.010 |
289 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −1.21 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Mo1 | 0.050872 (12) | 0.519055 (16) | 0.421732 (11) | 0.00874 (6) | |
Mo2 | −0.088778 (12) | 0.522183 (16) | 0.441491 (11) | 0.00876 (6) | |
Mo3 | −0.007917 (12) | 0.366634 (16) | 0.478971 (11) | 0.00892 (6) | |
Cl1 | 0.11919 (4) | 0.54599 (5) | 0.32044 (3) | 0.01566 (14) | |
Cl2 | −0.20765 (3) | 0.55673 (5) | 0.36800 (3) | 0.01437 (13) | |
Cl3 | −0.02055 (4) | 0.19090 (5) | 0.45114 (4) | 0.01621 (14) | |
Cl4 | −0.02895 (3) | 0.66392 (5) | 0.38961 (3) | 0.01189 (13) | |
Cl5 | −0.13876 (3) | 0.37565 (5) | 0.49929 (3) | 0.01174 (13) | |
Cl6 | 0.12389 (3) | 0.36952 (4) | 0.46138 (3) | 0.01160 (13) | |
Cl7 | −0.04240 (3) | 0.41385 (5) | 0.35073 (3) | 0.01179 (13) | |
O1 | −0.29081 (10) | 0.36002 (13) | 0.59683 (10) | 0.0146 (4) | |
O2 | −0.37390 (11) | 0.66348 (14) | 0.69485 (10) | 0.0167 (4) | |
O3 | −0.38274 (10) | 0.35869 (14) | 0.82754 (10) | 0.0153 (4) | |
C1 | −0.35013 (14) | 0.4602 (2) | 0.70579 (14) | 0.0129 (5) | |
C2 | −0.33433 (14) | 0.5109 (2) | 0.64497 (14) | 0.0135 (5) | |
C3 | −0.30655 (14) | 0.4590 (2) | 0.58929 (14) | 0.0142 (6) | |
C4 | −0.29515 (15) | 0.5081 (2) | 0.52694 (15) | 0.0172 (6) | |
H4 | −0.2793 | 0.4744 | 0.4885 | 0.021* | |
C5 | −0.30814 (15) | 0.6098 (2) | 0.52334 (15) | 0.0177 (6) | |
H5 | −0.3001 | 0.6430 | 0.4816 | 0.021* | |
C6 | −0.33248 (15) | 0.6641 (2) | 0.57888 (15) | 0.0175 (6) | |
H6 | −0.3386 | 0.7322 | 0.5752 | 0.021* | |
C7 | −0.34714 (14) | 0.6135 (2) | 0.63956 (14) | 0.0145 (5) | |
C8 | −0.37924 (15) | 0.5109 (2) | 0.76055 (14) | 0.0127 (5) | |
C9 | −0.39032 (15) | 0.6136 (2) | 0.75494 (14) | 0.0146 (6) | |
C10 | −0.41693 (16) | 0.6648 (2) | 0.81001 (15) | 0.0191 (6) | |
H10 | −0.4232 | 0.7329 | 0.8078 | 0.023* | |
C11 | −0.43409 (16) | 0.6105 (2) | 0.86891 (15) | 0.0196 (6) | |
H11 | −0.4527 | 0.6445 | 0.9058 | 0.024* | |
C12 | −0.42508 (16) | 0.5082 (2) | 0.87612 (15) | 0.0170 (6) | |
H12 | −0.4382 | 0.4748 | 0.9160 | 0.020* | |
C13 | −0.39594 (15) | 0.4586 (2) | 0.82168 (15) | 0.0140 (5) | |
C14 | −0.33509 (14) | 0.3594 (2) | 0.71291 (14) | 0.0133 (5) | |
C15 | −0.35026 (15) | 0.3097 (2) | 0.77502 (14) | 0.0143 (5) | |
C16 | −0.33338 (15) | 0.2107 (2) | 0.78344 (15) | 0.0169 (6) | |
H16 | −0.3439 | 0.1760 | 0.8237 | 0.020* | |
C17 | −0.30006 (15) | 0.1646 (2) | 0.72952 (15) | 0.0163 (6) | |
H17 | −0.2880 | 0.0980 | 0.7352 | 0.020* | |
C18 | −0.28375 (15) | 0.2126 (2) | 0.66731 (15) | 0.0166 (6) | |
H18 | −0.2607 | 0.1794 | 0.6330 | 0.020* | |
C19 | −0.30282 (14) | 0.3101 (2) | 0.65858 (14) | 0.0142 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mo1 | 0.00966 (11) | 0.00890 (12) | 0.00809 (11) | 0.00078 (8) | 0.00280 (8) | 0.00075 (8) |
Mo2 | 0.00910 (11) | 0.00898 (12) | 0.00841 (11) | 0.00116 (8) | 0.00194 (9) | 0.00080 (8) |
Mo3 | 0.01010 (11) | 0.00791 (11) | 0.00914 (11) | 0.00078 (8) | 0.00268 (9) | 0.00043 (8) |
Cl1 | 0.0183 (3) | 0.0175 (3) | 0.0127 (3) | −0.0004 (3) | 0.0076 (3) | 0.0012 (2) |
Cl2 | 0.0125 (3) | 0.0172 (3) | 0.0131 (3) | 0.0030 (3) | 0.0005 (2) | 0.0001 (2) |
Cl3 | 0.0196 (3) | 0.0102 (3) | 0.0195 (3) | 0.0002 (3) | 0.0049 (3) | −0.0019 (3) |
Cl4 | 0.0135 (3) | 0.0109 (3) | 0.0116 (3) | 0.0018 (2) | 0.0030 (2) | 0.0032 (2) |
Cl5 | 0.0114 (3) | 0.0114 (3) | 0.0128 (3) | −0.0012 (2) | 0.0030 (2) | 0.0002 (2) |
Cl6 | 0.0119 (3) | 0.0120 (3) | 0.0116 (3) | 0.0026 (2) | 0.0038 (2) | 0.0003 (2) |
Cl7 | 0.0131 (3) | 0.0131 (3) | 0.0094 (3) | 0.0002 (2) | 0.0019 (2) | −0.0014 (2) |
O1 | 0.0171 (10) | 0.0153 (10) | 0.0121 (9) | 0.0011 (8) | 0.0044 (8) | −0.0003 (7) |
O2 | 0.0227 (10) | 0.0142 (10) | 0.0141 (9) | 0.0060 (8) | 0.0059 (8) | 0.0022 (8) |
O3 | 0.0203 (10) | 0.0151 (10) | 0.0115 (9) | −0.0008 (8) | 0.0065 (8) | 0.0005 (7) |
C1 | 0.0081 (12) | 0.0176 (14) | 0.0123 (13) | 0.0001 (10) | −0.0013 (10) | 0.0003 (10) |
C2 | 0.0097 (12) | 0.0182 (14) | 0.0123 (13) | 0.0006 (11) | 0.0005 (10) | 0.0009 (11) |
C3 | 0.0117 (13) | 0.0164 (14) | 0.0138 (13) | −0.0011 (11) | −0.0013 (11) | 0.0013 (10) |
C4 | 0.0138 (13) | 0.0252 (15) | 0.0129 (14) | 0.0037 (12) | 0.0031 (11) | 0.0008 (11) |
C5 | 0.0150 (13) | 0.0257 (15) | 0.0129 (13) | 0.0045 (12) | 0.0039 (11) | 0.0080 (12) |
C6 | 0.0147 (13) | 0.0187 (15) | 0.0191 (14) | 0.0046 (11) | 0.0024 (11) | 0.0055 (11) |
C7 | 0.0112 (13) | 0.0184 (14) | 0.0138 (13) | 0.0024 (11) | 0.0018 (10) | 0.0007 (11) |
C8 | 0.0117 (13) | 0.0149 (14) | 0.0113 (13) | 0.0016 (10) | 0.0008 (10) | 0.0006 (10) |
C9 | 0.0138 (13) | 0.0173 (14) | 0.0130 (13) | 0.0025 (11) | 0.0028 (11) | 0.0028 (11) |
C10 | 0.0211 (15) | 0.0167 (14) | 0.0196 (15) | 0.0067 (12) | 0.0035 (12) | 0.0005 (12) |
C11 | 0.0208 (15) | 0.0235 (16) | 0.0152 (14) | 0.0041 (12) | 0.0048 (12) | −0.0042 (12) |
C12 | 0.0167 (14) | 0.0214 (15) | 0.0139 (13) | −0.0008 (12) | 0.0056 (11) | 0.0016 (11) |
C13 | 0.0127 (13) | 0.0147 (14) | 0.0146 (13) | −0.0009 (11) | 0.0014 (11) | −0.0001 (10) |
C14 | 0.0122 (13) | 0.0141 (13) | 0.0135 (13) | −0.0017 (10) | 0.0013 (10) | −0.0007 (10) |
C15 | 0.0142 (13) | 0.0172 (14) | 0.0111 (12) | −0.0024 (11) | 0.0006 (10) | −0.0023 (11) |
C16 | 0.0193 (14) | 0.0149 (14) | 0.0165 (14) | −0.0039 (11) | 0.0021 (11) | 0.0010 (11) |
C17 | 0.0173 (14) | 0.0113 (13) | 0.0191 (14) | 0.0002 (11) | −0.0013 (11) | −0.0024 (11) |
C18 | 0.0175 (14) | 0.0164 (14) | 0.0154 (13) | 0.0007 (11) | 0.0000 (11) | −0.0049 (11) |
C19 | 0.0127 (13) | 0.0184 (14) | 0.0110 (12) | −0.0020 (11) | −0.0001 (10) | −0.0004 (11) |
Geometric parameters (Å, º) top
Mo1—Cl1 | 2.4309 (9) | O1—C3 | 1.374 (3) |
Mo1—Cl7 | 2.4596 (8) | O1—C19 | 1.380 (3) |
Mo1—Cl4 | 2.4655 (7) | O2—C9 | 1.378 (3) |
Mo1—Cl5i | 2.4735 (8) | O2—C7 | 1.379 (3) |
Mo1—Cl6 | 2.4785 (7) | O3—C15 | 1.383 (3) |
Mo1—Mo2i | 2.6133 (7) | O3—C13 | 1.376 (3) |
Mo1—Mo3i | 2.6168 (5) | C1—C2 | 1.391 (4) |
Mo1—Mo2 | 2.6192 (6) | C1—C8 | 1.396 (4) |
Mo1—Mo3 | 2.6198 (5) | C1—C14 | 1.394 (4) |
Mo2—Cl2 | 2.4427 (10) | C2—C3 | 1.406 (4) |
Mo2—Cl4 | 2.4698 (8) | C2—C7 | 1.410 (4) |
Mo2—Cl7 | 2.4765 (8) | C3—C4 | 1.381 (4) |
Mo2—Cl6i | 2.4841 (8) | C4—C5 | 1.398 (4) |
Mo2—Cl5 | 2.4902 (8) | C5—C6 | 1.393 (4) |
Mo2—Mo3 | 2.6093 (5) | C6—C7 | 1.382 (4) |
Mo2—Mo1i | 2.6132 (7) | C8—C9 | 1.406 (4) |
Mo2—Mo3i | 2.6174 (7) | C8—C13 | 1.412 (4) |
Mo3—Cl3 | 2.4397 (8) | C9—C10 | 1.382 (4) |
Mo3—Cl5 | 2.4662 (8) | C10—C11 | 1.394 (4) |
Mo3—Cl6 | 2.4667 (8) | C11—C12 | 1.400 (4) |
Mo3—Cl7 | 2.4750 (8) | C12—C13 | 1.384 (4) |
Mo3—Cl4i | 2.4886 (8) | C14—C15 | 1.401 (4) |
Mo3—Mo1i | 2.6168 (5) | C14—C19 | 1.409 (4) |
Mo3—Mo2i | 2.6174 (7) | C15—C16 | 1.379 (4) |
Cl4—Mo3i | 2.4886 (8) | C16—C17 | 1.393 (4) |
Cl5—Mo1i | 2.4733 (9) | C17—C18 | 1.399 (4) |
Cl6—Mo2i | 2.4841 (7) | C18—C19 | 1.369 (4) |
| | | |
Cl1—Mo1—Cl7 | 93.24 (3) | Cl7—Mo3—Cl4i | 174.56 (2) |
Cl1—Mo1—Cl4 | 92.23 (3) | Cl3—Mo3—Mo2 | 134.18 (2) |
Cl7—Mo1—Cl4 | 89.41 (3) | Cl5—Mo3—Mo2 | 58.682 (18) |
Cl1—Mo1—Cl5i | 91.11 (3) | Cl6—Mo3—Mo2 | 118.335 (19) |
Cl7—Mo1—Cl5i | 175.61 (2) | Cl7—Mo3—Mo2 | 58.23 (2) |
Cl4—Mo1—Cl5i | 89.86 (3) | Cl4i—Mo3—Mo2 | 117.66 (2) |
Cl1—Mo1—Cl6 | 92.53 (3) | Cl3—Mo3—Mo1i | 134.37 (2) |
Cl7—Mo1—Cl6 | 89.42 (3) | Cl5—Mo3—Mo1i | 58.14 (2) |
Cl4—Mo1—Cl6 | 175.15 (2) | Cl6—Mo3—Mo1i | 118.45 (3) |
Cl5i—Mo1—Cl6 | 90.95 (3) | Cl7—Mo3—Mo1i | 118.20 (2) |
Cl1—Mo1—Mo2i | 134.31 (2) | Cl4i—Mo3—Mo1i | 57.687 (19) |
Cl7—Mo1—Mo2i | 118.23 (3) | Mo2—Mo3—Mo1i | 60.003 (16) |
Cl4—Mo1—Mo2i | 118.37 (2) | Cl3—Mo3—Mo2i | 135.90 (2) |
Cl5i—Mo1—Mo2i | 58.54 (2) | Cl5—Mo3—Mo2i | 118.19 (2) |
Cl6—Mo1—Mo2i | 58.33 (2) | Cl6—Mo3—Mo2i | 58.41 (2) |
Cl1—Mo1—Mo3i | 134.27 (2) | Cl7—Mo3—Mo2i | 117.50 (3) |
Cl7—Mo1—Mo3i | 118.24 (2) | Cl4i—Mo3—Mo2i | 57.79 (2) |
Cl4—Mo1—Mo3i | 58.55 (2) | Mo2—Mo3—Mo2i | 89.91 (2) |
Cl5i—Mo1—Mo3i | 57.88 (2) | Mo1i—Mo3—Mo2i | 60.054 (16) |
Cl6—Mo1—Mo3i | 118.15 (2) | Cl3—Mo3—Mo1 | 135.49 (2) |
Mo2i—Mo1—Mo3i | 59.855 (14) | Cl5—Mo3—Mo1 | 118.78 (2) |
Cl1—Mo1—Mo2 | 135.90 (3) | Cl6—Mo3—Mo1 | 58.230 (19) |
Cl7—Mo1—Mo2 | 58.27 (2) | Cl7—Mo3—Mo1 | 57.65 (2) |
Cl4—Mo1—Mo2 | 58.025 (18) | Cl4i—Mo3—Mo1 | 117.63 (2) |
Cl5i—Mo1—Mo2 | 117.85 (2) | Mo2—Mo3—Mo1 | 60.118 (16) |
Cl6—Mo1—Mo2 | 117.52 (2) | Mo1i—Mo3—Mo1 | 90.13 (2) |
Mo2i—Mo1—Mo2 | 89.78 (3) | Mo2i—Mo3—Mo1 | 59.865 (14) |
Mo3i—Mo1—Mo2 | 59.98 (2) | Mo1—Cl4—Mo2 | 64.11 (2) |
Cl1—Mo1—Mo3 | 135.85 (2) | Mo1—Cl4—Mo3i | 63.77 (2) |
Cl7—Mo1—Mo3 | 58.22 (2) | Mo2—Cl4—Mo3i | 63.72 (2) |
Cl4—Mo1—Mo3 | 117.76 (2) | Mo3—Cl5—Mo1i | 63.98 (2) |
Cl5i—Mo1—Mo3 | 118.54 (2) | Mo3—Cl5—Mo2 | 63.53 (2) |
Cl6—Mo1—Mo3 | 57.79 (2) | Mo1i—Cl5—Mo2 | 63.54 (2) |
Mo2i—Mo1—Mo3 | 60.022 (15) | Mo3—Cl6—Mo1 | 63.979 (19) |
Mo3i—Mo1—Mo3 | 89.87 (2) | Mo3—Cl6—Mo2i | 63.83 (3) |
Mo2—Mo1—Mo3 | 59.742 (14) | Mo1—Cl6—Mo2i | 63.55 (2) |
Cl2—Mo2—Cl4 | 92.01 (2) | Mo1—Cl7—Mo3 | 64.13 (2) |
Cl2—Mo2—Cl7 | 95.05 (3) | Mo1—Cl7—Mo2 | 64.09 (2) |
Cl4—Mo2—Cl7 | 88.92 (3) | Mo3—Cl7—Mo2 | 63.60 (2) |
Cl2—Mo2—Cl6i | 90.01 (3) | C3—O1—C19 | 120.6 (2) |
Cl4—Mo2—Cl6i | 89.98 (3) | C9—O2—C7 | 120.5 (2) |
Cl7—Mo2—Cl6i | 174.86 (2) | C15—O3—C13 | 120.2 (2) |
Cl2—Mo2—Cl5 | 92.74 (2) | C2—C1—C8 | 119.8 (2) |
Cl4—Mo2—Cl5 | 175.23 (2) | C2—C1—C14 | 120.1 (2) |
Cl7—Mo2—Cl5 | 90.25 (3) | C8—C1—C14 | 120.1 (2) |
Cl6i—Mo2—Cl5 | 90.43 (3) | C1—C2—C3 | 119.6 (2) |
Cl2—Mo2—Mo3 | 136.77 (2) | C1—C2—C7 | 119.6 (2) |
Cl4—Mo2—Mo3 | 118.00 (2) | C3—C2—C7 | 120.8 (2) |
Cl7—Mo2—Mo3 | 58.17 (2) | O1—C3—C4 | 120.1 (2) |
Cl6i—Mo2—Mo3 | 118.23 (2) | O1—C3—C2 | 120.2 (2) |
Cl5—Mo2—Mo3 | 57.79 (2) | C4—C3—C2 | 119.7 (3) |
Cl2—Mo2—Mo1i | 133.18 (3) | C3—C4—C5 | 118.1 (3) |
Cl4—Mo2—Mo1i | 118.58 (2) | C6—C5—C4 | 123.6 (3) |
Cl7—Mo2—Mo1i | 118.28 (2) | C7—C6—C5 | 117.8 (3) |
Cl6i—Mo2—Mo1i | 58.122 (19) | C6—C7—O2 | 120.0 (2) |
Cl5—Mo2—Mo1i | 57.919 (19) | C6—C7—C2 | 119.9 (3) |
Mo3—Mo2—Mo1i | 60.140 (16) | O2—C7—C2 | 120.1 (2) |
Cl2—Mo2—Mo3i | 133.09 (2) | C1—C8—C9 | 119.8 (2) |
Cl4—Mo2—Mo3i | 58.490 (19) | C1—C8—C13 | 119.4 (2) |
Cl7—Mo2—Mo3i | 117.59 (2) | C9—C8—C13 | 120.8 (2) |
Cl6i—Mo2—Mo3i | 57.76 (2) | C10—C9—O2 | 119.9 (2) |
Cl5—Mo2—Mo3i | 118.00 (2) | C10—C9—C8 | 120.1 (3) |
Mo3—Mo2—Mo3i | 90.09 (2) | O2—C9—C8 | 120.0 (2) |
Mo1i—Mo2—Mo3i | 60.11 (2) | C9—C10—C11 | 117.6 (3) |
Cl2—Mo2—Mo1 | 136.54 (2) | C10—C11—C12 | 124.2 (3) |
Cl4—Mo2—Mo1 | 57.867 (19) | C13—C12—C11 | 117.5 (3) |
Cl7—Mo2—Mo1 | 57.64 (2) | O3—C13—C12 | 119.9 (2) |
Cl6i—Mo2—Mo1 | 117.71 (3) | O3—C13—C8 | 120.2 (2) |
Cl5—Mo2—Mo1 | 117.91 (2) | C12—C13—C8 | 119.9 (2) |
Mo3—Mo2—Mo1 | 60.140 (12) | C15—C14—C1 | 119.4 (2) |
Mo1i—Mo2—Mo1 | 90.22 (3) | C15—C14—C19 | 121.2 (2) |
Mo3i—Mo2—Mo1 | 59.962 (16) | C1—C14—C19 | 119.4 (2) |
Cl3—Mo3—Cl5 | 90.94 (2) | O3—C15—C16 | 119.7 (2) |
Cl3—Mo3—Cl6 | 92.97 (2) | O3—C15—C14 | 120.6 (2) |
Cl5—Mo3—Cl6 | 176.07 (2) | C16—C15—C14 | 119.7 (2) |
Cl3—Mo3—Cl7 | 92.40 (2) | C15—C16—C17 | 117.8 (3) |
Cl5—Mo3—Cl7 | 90.84 (4) | C16—C17—C18 | 123.7 (3) |
Cl6—Mo3—Cl7 | 89.34 (3) | C19—C18—C17 | 117.9 (3) |
Cl3—Mo3—Cl4i | 93.02 (2) | C18—C19—O1 | 120.3 (2) |
Cl5—Mo3—Cl4i | 89.50 (4) | C18—C19—C14 | 119.7 (3) |
Cl6—Mo3—Cl4i | 89.95 (4) | O1—C19—C14 | 120.0 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
(10) Bis(4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium)
dithionate
top
Crystal data top
C19H9O3·O3S | V = 689.8 (2) Å3 |
Mr = 365.32 | Z = 2 |
Triclinic, P1 | F(000) = 374 |
Hall symbol: -P 1 | Dx = 1.759 Mg m−3 |
a = 8.6300 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9680 (18) Å | µ = 0.28 mm−1 |
c = 9.876 (2) Å | T = 120 K |
α = 97.91 (3)° | Plate, orange |
β = 102.37 (3)° | 0.50 × 0.33 × 0.20 mm |
γ = 108.61 (3)° | |
Data collection top
Siemens SMART CCD diffractometer | 2779 independent reflections |
Radiation source: fine-focus sealed tube | 2452 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 2.2° |
ω scan, frame data integration | h = −10→10 |
Absorption correction: empirical (using intensity measurements) | k = −11→11 |
Tmin = 0.616, Tmax = 0.962 | l = −12→12 |
5953 measured reflections | |
Refinement top
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Calculated w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1004P] where P = (Fo2 + 2Fc2)/3 |
2779 reflections | (Δ/σ)max = 0.002 |
235 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | −0.09095 (4) | −0.08812 (4) | 0.03601 (4) | 0.01374 (12) | |
O7 | −0.25338 (14) | −0.07534 (14) | −0.02557 (13) | 0.0254 (3) | |
O8 | −0.03366 (15) | −0.03780 (14) | 0.18974 (12) | 0.0286 (3) | |
O9 | −0.08044 (15) | −0.24187 (13) | −0.01992 (13) | 0.0255 (3) | |
O1 | −0.37974 (13) | −0.38610 (12) | 0.14184 (11) | 0.0171 (2) | |
O2 | −0.49125 (14) | −0.83946 (12) | 0.36618 (11) | 0.0189 (2) | |
O3 | −0.82405 (13) | −0.49878 (13) | 0.37918 (12) | 0.0189 (2) | |
C1 | −0.56952 (18) | −0.57924 (17) | 0.28984 (15) | 0.0147 (3) | |
C2 | −0.43809 (19) | −0.61505 (17) | 0.25103 (15) | 0.0153 (3) | |
C3 | −0.34140 (19) | −0.51602 (17) | 0.17734 (15) | 0.0163 (3) | |
C4 | −0.20936 (19) | −0.54894 (19) | 0.13989 (16) | 0.0197 (3) | |
H4 | −0.1429 | −0.4833 | 0.0929 | 0.024* | |
C5 | −0.17824 (19) | −0.6845 (2) | 0.17483 (17) | 0.0215 (3) | |
H5 | −0.0911 | −0.7092 | 0.1475 | 0.026* | |
C6 | −0.2710 (2) | −0.78490 (18) | 0.24865 (17) | 0.0208 (3) | |
H6 | −0.2462 | −0.8739 | 0.2703 | 0.025* | |
C7 | −0.39998 (19) | −0.74797 (17) | 0.28820 (16) | 0.0171 (3) | |
C8 | −0.66195 (19) | −0.67269 (17) | 0.36837 (15) | 0.0160 (3) | |
C9 | −0.61880 (19) | −0.80211 (17) | 0.40795 (16) | 0.0172 (3) | |
C10 | −0.7001 (2) | −0.88712 (18) | 0.49493 (17) | 0.0215 (3) | |
H10 | −0.6737 | −0.9734 | 0.5219 | 0.026* | |
C11 | −0.8226 (2) | −0.84029 (18) | 0.54116 (16) | 0.0219 (3) | |
H11 | −0.8761 | −0.8964 | 0.6009 | 0.026* | |
C12 | −0.8691 (2) | −0.71312 (19) | 0.50226 (16) | 0.0208 (3) | |
H12 | −0.9524 | −0.6857 | 0.5342 | 0.025* | |
C13 | −0.78726 (19) | −0.62956 (17) | 0.41471 (16) | 0.0171 (3) | |
C14 | −0.60521 (18) | −0.44509 (17) | 0.25648 (15) | 0.0151 (3) | |
C15 | −0.73563 (19) | −0.40754 (17) | 0.29924 (16) | 0.0167 (3) | |
C16 | −0.7746 (2) | −0.27802 (18) | 0.26240 (17) | 0.0199 (3) | |
H16 | −0.8625 | −0.2527 | 0.2877 | 0.024* | |
C17 | −0.6775 (2) | −0.18627 (17) | 0.18595 (16) | 0.0199 (3) | |
H17 | −0.7042 | −0.0997 | 0.1600 | 0.024* | |
C18 | −0.5433 (2) | −0.21684 (17) | 0.14640 (16) | 0.0184 (3) | |
H18 | −0.4794 | −0.1508 | 0.0981 | 0.022* | |
C19 | −0.50842 (18) | −0.34897 (17) | 0.18146 (15) | 0.0157 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01485 (19) | 0.01360 (19) | 0.0152 (2) | 0.00554 (14) | 0.00625 (14) | 0.00659 (13) |
O7 | 0.0167 (6) | 0.0273 (6) | 0.0388 (7) | 0.0097 (5) | 0.0102 (5) | 0.0201 (5) |
O8 | 0.0323 (7) | 0.0318 (7) | 0.0149 (6) | 0.0009 (5) | 0.0079 (5) | 0.0077 (5) |
O9 | 0.0295 (6) | 0.0151 (6) | 0.0396 (7) | 0.0090 (5) | 0.0209 (6) | 0.0106 (5) |
O1 | 0.0186 (5) | 0.0153 (5) | 0.0170 (5) | 0.0045 (4) | 0.0057 (4) | 0.0053 (4) |
O2 | 0.0231 (6) | 0.0148 (5) | 0.0191 (6) | 0.0072 (4) | 0.0042 (5) | 0.0063 (4) |
O3 | 0.0189 (5) | 0.0191 (5) | 0.0199 (5) | 0.0072 (4) | 0.0069 (4) | 0.0052 (4) |
C1 | 0.0152 (7) | 0.0119 (7) | 0.0106 (7) | 0.0008 (6) | −0.0015 (6) | −0.0001 (6) |
C2 | 0.0158 (7) | 0.0130 (7) | 0.0124 (7) | 0.0026 (6) | 0.0000 (6) | 0.0001 (6) |
C3 | 0.0185 (7) | 0.0136 (7) | 0.0122 (7) | 0.0033 (6) | 0.0006 (6) | 0.0002 (6) |
C4 | 0.0178 (7) | 0.0223 (8) | 0.0143 (7) | 0.0035 (6) | 0.0033 (6) | 0.0001 (6) |
C5 | 0.0177 (8) | 0.0254 (8) | 0.0168 (8) | 0.0083 (6) | 0.0000 (6) | −0.0040 (6) |
C6 | 0.0218 (8) | 0.0177 (7) | 0.0195 (8) | 0.0091 (6) | −0.0008 (6) | −0.0011 (6) |
C7 | 0.0193 (7) | 0.0142 (7) | 0.0133 (7) | 0.0036 (6) | 0.0006 (6) | 0.0011 (6) |
C8 | 0.0172 (7) | 0.0136 (7) | 0.0116 (7) | 0.0013 (6) | 0.0003 (6) | 0.0014 (6) |
C9 | 0.0184 (7) | 0.0139 (7) | 0.0137 (7) | 0.0020 (6) | −0.0002 (6) | 0.0013 (6) |
C10 | 0.0257 (8) | 0.0149 (7) | 0.0156 (7) | 0.0000 (6) | −0.0010 (6) | 0.0049 (6) |
C11 | 0.0218 (8) | 0.0195 (8) | 0.0145 (7) | −0.0037 (6) | 0.0020 (6) | 0.0045 (6) |
C12 | 0.0175 (7) | 0.0232 (8) | 0.0146 (7) | 0.0005 (6) | 0.0030 (6) | 0.0002 (6) |
C13 | 0.0165 (7) | 0.0149 (7) | 0.0149 (7) | 0.0024 (6) | 0.0001 (6) | 0.0021 (6) |
C14 | 0.0157 (7) | 0.0130 (7) | 0.0125 (7) | 0.0031 (6) | −0.0005 (6) | 0.0012 (6) |
C15 | 0.0163 (7) | 0.0150 (7) | 0.0144 (7) | 0.0027 (6) | 0.0011 (6) | 0.0017 (6) |
C16 | 0.0193 (8) | 0.0179 (7) | 0.0198 (8) | 0.0085 (6) | 0.0003 (6) | −0.0005 (6) |
C17 | 0.0243 (8) | 0.0123 (7) | 0.0172 (7) | 0.0062 (6) | −0.0037 (6) | 0.0006 (6) |
C18 | 0.0224 (8) | 0.0132 (7) | 0.0134 (7) | 0.0019 (6) | −0.0005 (6) | 0.0028 (6) |
C19 | 0.0161 (7) | 0.0143 (7) | 0.0121 (7) | 0.0028 (6) | 0.0001 (6) | 0.0008 (6) |
Geometric parameters (Å, º) top
S1—O8 | 1.4493 (12) | C4—C5 | 1.397 (2) |
S1—O7 | 1.4507 (12) | C5—C6 | 1.398 (2) |
S1—O9 | 1.4512 (12) | C6—C7 | 1.374 (2) |
S1—S1i | 2.1616 (10) | C8—C13 | 1.400 (2) |
O1—C19 | 1.3724 (18) | C8—C9 | 1.406 (2) |
O1—C3 | 1.3779 (18) | C9—C10 | 1.381 (2) |
O2—C9 | 1.3733 (19) | C10—C11 | 1.393 (2) |
O2—C7 | 1.3813 (18) | C11—C12 | 1.399 (2) |
O3—C13 | 1.3793 (18) | C12—C13 | 1.382 (2) |
O3—C15 | 1.3829 (18) | C14—C15 | 1.402 (2) |
C1—C2 | 1.386 (2) | C14—C19 | 1.404 (2) |
C1—C14 | 1.397 (2) | C15—C16 | 1.381 (2) |
C1—C8 | 1.399 (2) | C16—C17 | 1.397 (2) |
C2—C3 | 1.407 (2) | C17—C18 | 1.391 (2) |
C2—C7 | 1.408 (2) | C18—C19 | 1.382 (2) |
C3—C4 | 1.374 (2) | | |
| | | |
O8—S1—O7 | 113.75 (8) | C1—C8—C13 | 119.76 (13) |
O8—S1—O9 | 114.14 (8) | C1—C8—C9 | 119.11 (14) |
O7—S1—O9 | 113.22 (8) | C13—C8—C9 | 120.98 (14) |
O8—S1—S1i | 104.55 (6) | O2—C9—C10 | 119.94 (13) |
O7—S1—S1i | 104.83 (5) | O2—C9—C8 | 120.42 (13) |
O9—S1—S1i | 105.05 (5) | C10—C9—C8 | 119.57 (14) |
C19—O1—C3 | 120.65 (12) | C9—C10—C11 | 118.29 (14) |
C9—O2—C7 | 120.69 (11) | C10—C11—C12 | 123.30 (14) |
C13—O3—C15 | 120.29 (12) | C13—C12—C11 | 117.78 (14) |
C2—C1—C14 | 120.15 (13) | O3—C13—C12 | 119.52 (14) |
C2—C1—C8 | 120.18 (13) | O3—C13—C8 | 120.34 (13) |
C14—C1—C8 | 119.60 (14) | C12—C13—C8 | 120.07 (14) |
C1—C2—C3 | 119.63 (13) | C1—C14—C15 | 119.74 (13) |
C1—C2—C7 | 119.85 (14) | C1—C14—C19 | 119.28 (14) |
C3—C2—C7 | 120.50 (14) | C15—C14—C19 | 120.97 (13) |
C4—C3—O1 | 119.84 (13) | C16—C15—O3 | 120.03 (14) |
C4—C3—C2 | 120.21 (14) | C16—C15—C14 | 119.77 (14) |
O1—C3—C2 | 119.95 (13) | O3—C15—C14 | 120.20 (13) |
C3—C4—C5 | 117.75 (14) | C15—C16—C17 | 117.79 (14) |
C4—C5—C6 | 123.56 (14) | C18—C17—C16 | 123.82 (13) |
C7—C6—C5 | 117.89 (14) | C19—C18—C17 | 117.62 (14) |
C6—C7—O2 | 120.26 (13) | O1—C19—C18 | 119.72 (13) |
C6—C7—C2 | 120.04 (14) | O1—C19—C14 | 120.31 (13) |
O2—C7—C2 | 119.70 (13) | C18—C19—C14 | 119.96 (14) |
Symmetry code: (i) −x, −y, −z. |
(11) 2,6,10-tri-
tert-butyl-4,8,12-trioxa-4,8,12,12
c-tetrahydro-
dibenzo[cd,mn]pyrenium hexafluorophosphate acetonitrile
top
Crystal data top
C31H33O3·F6P·C2H3N | Z = 4 |
Mr = 639.60 | F(000) = 1336 |
Monoclinic, P21/n | Dx = 1.386 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.085 (2) Å | µ = 0.16 mm−1 |
b = 11.347 (2) Å | T = 120 K |
c = 22.930 (5) Å | Plate, orange |
β = 102.87 (3)° | 0.48 × 0.40 × 0.15 mm |
V = 3065.4 (11) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 6252 independent reflections |
Radiation source: fine-focus sealed tube | 5092 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
ω scan, frame data integration | h = −15→15 |
Absorption correction: empirical (using intensity measurements) | k = −14→14 |
Tmin = 0.853, Tmax = 0.978 | l = −28→28 |
31555 measured reflections | |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.0441P)2 + 1.7107P] where P = (Fo2 + 2Fc2)/3 |
6252 reflections | (Δ/σ)max = 0.054 |
434 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.34656 (3) | 0.41333 (4) | 0.101226 (17) | 0.02354 (11) | |
F1 | 0.29677 (10) | 0.32970 (9) | 0.04514 (4) | 0.0405 (3) | |
F2 | 0.46557 (9) | 0.34492 (9) | 0.11102 (5) | 0.0449 (3) | |
F3 | 0.22908 (9) | 0.48232 (10) | 0.09040 (6) | 0.0463 (3) | |
F4 | 0.38972 (9) | 0.50418 (9) | 0.05780 (5) | 0.0417 (3) | |
F5 | 0.39743 (11) | 0.49646 (11) | 0.15628 (5) | 0.0546 (3) | |
F6 | 0.30390 (12) | 0.32194 (11) | 0.14362 (5) | 0.0555 (3) | |
O1 | −0.46862 (8) | 0.22621 (9) | −0.08095 (4) | 0.0194 (2) | |
O2 | −0.75326 (8) | 0.06305 (9) | 0.01318 (4) | 0.0200 (2) | |
O3 | −0.37139 (8) | 0.12015 (9) | 0.12786 (4) | 0.0188 (2) | |
C1 | −0.53172 (12) | 0.13935 (12) | 0.02060 (6) | 0.0166 (3) | |
C2 | −0.61116 (12) | 0.14647 (12) | −0.03352 (6) | 0.0171 (3) | |
C3 | −0.57861 (12) | 0.18952 (12) | −0.08450 (6) | 0.0181 (3) | |
C4 | −0.65619 (13) | 0.19360 (13) | −0.13862 (6) | 0.0210 (3) | |
H4 | −0.6352 | 0.2231 | −0.1724 | 0.025* | |
C5 | −0.76712 (13) | 0.15266 (13) | −0.14209 (7) | 0.0221 (3) | |
C6 | −0.80038 (12) | 0.11075 (13) | −0.09060 (7) | 0.0215 (3) | |
H6 | −0.8745 | 0.0855 | −0.0930 | 0.026* | |
C7 | −0.72266 (12) | 0.10755 (13) | −0.03697 (6) | 0.0188 (3) | |
C8 | −0.56226 (12) | 0.09261 (12) | 0.07064 (6) | 0.0167 (3) | |
C9 | −0.67409 (12) | 0.05414 (13) | 0.06657 (6) | 0.0181 (3) | |
C10 | −0.70406 (12) | 0.00474 (13) | 0.11556 (7) | 0.0209 (3) | |
H10 | −0.7780 | −0.0209 | 0.1131 | 0.025* | |
C11 | −0.62246 (13) | −0.00680 (13) | 0.16937 (7) | 0.0212 (3) | |
C12 | −0.51048 (12) | 0.03404 (13) | 0.17420 (6) | 0.0199 (3) | |
H12 | −0.4572 | 0.0280 | 0.2102 | 0.024* | |
C13 | −0.48143 (12) | 0.08286 (12) | 0.12474 (6) | 0.0172 (3) | |
C14 | −0.42035 (12) | 0.17520 (12) | 0.02379 (6) | 0.0165 (3) | |
C15 | −0.34000 (12) | 0.16487 (12) | 0.07793 (6) | 0.0172 (3) | |
C16 | −0.22893 (12) | 0.19625 (13) | 0.08075 (6) | 0.0196 (3) | |
H16 | −0.1755 | 0.1913 | 0.1168 | 0.023* | |
C17 | −0.19662 (12) | 0.23599 (12) | 0.02861 (7) | 0.0196 (3) | |
C18 | −0.27771 (12) | 0.24856 (13) | −0.02539 (6) | 0.0194 (3) | |
H18 | −0.2566 | 0.2773 | −0.0593 | 0.023* | |
C19 | −0.38880 (12) | 0.21785 (12) | −0.02762 (6) | 0.0174 (3) | |
C20 | −0.85462 (14) | 0.14830 (15) | −0.20174 (7) | 0.0278 (4) | |
C21 | −0.81103 (15) | 0.20551 (16) | −0.25274 (7) | 0.0328 (4) | |
H21A | −0.8685 | 0.2006 | −0.2891 | 0.049* | |
H21B | −0.7440 | 0.1651 | −0.2578 | 0.049* | |
H21C | −0.7933 | 0.2867 | −0.2433 | 0.049* | |
C22 | −0.96215 (16) | 0.2141 (2) | −0.19535 (9) | 0.0433 (5) | |
H22A | −1.0175 | 0.2109 | −0.2325 | 0.065* | |
H22B | −0.9437 | 0.2949 | −0.1850 | 0.065* | |
H22C | −0.9926 | 0.1779 | −0.1645 | 0.065* | |
C23 | −0.88260 (16) | 0.01823 (17) | −0.21726 (7) | 0.0364 (4) | |
H23A | −0.9377 | 0.0134 | −0.2545 | 0.055* | |
H23B | −0.9128 | −0.0175 | −0.1861 | 0.055* | |
H23C | −0.8148 | −0.0225 | −0.2208 | 0.055* | |
C24 | −0.65476 (16) | −0.06527 (16) | 0.22341 (7) | 0.0331 (4) | |
C25 | −0.7698 (3) | −0.1145 (3) | 0.21274 (12) | 0.0346 (8) | 0.647 (4) |
H25A | −0.7820 | −0.1491 | 0.2490 | 0.052* | 0.65 |
H25B | −0.7785 | −0.1737 | 0.1822 | 0.052* | 0.65 |
H25C | −0.8243 | −0.0528 | 0.2001 | 0.052* | 0.65 |
C26 | −0.5685 (3) | −0.1779 (3) | 0.24179 (13) | 0.0363 (8) | 0.647 (4) |
H26A | −0.4913 | −0.1510 | 0.2493 | 0.055* | 0.65 |
H26B | −0.5814 | −0.2340 | 0.2096 | 0.055* | 0.65 |
H26C | −0.5824 | −0.2146 | 0.2772 | 0.055* | 0.65 |
C27 | −0.6281 (3) | 0.0164 (3) | 0.27750 (12) | 0.0340 (8) | 0.647 (4) |
H27A | −0.5520 | 0.0457 | 0.2826 | 0.051* | 0.65 |
H27B | −0.6350 | −0.0264 | 0.3126 | 0.051* | 0.65 |
H27C | −0.6804 | 0.0812 | 0.2714 | 0.051* | 0.65 |
C25U | −0.7159 (5) | −0.1793 (5) | 0.2033 (2) | 0.0319 (13) | 0.353 (4) |
H25D | −0.785 (5) | −0.182 (5) | 0.168 (3) | 0.048* | 0.353 (4) |
H25E | −0.745 (5) | −0.211 (5) | 0.242 (3) | 0.048* | 0.353 (4) |
H25F | −0.652 (5) | −0.242 (5) | 0.194 (3) | 0.048* | 0.353 (4) |
C26U | −0.5761 (5) | −0.0654 (6) | 0.2765 (2) | 0.0385 (16) | 0.353 (4) |
H26D | −0.5431 | 0.0117 | 0.2838 | 0.058* | 0.35 |
H26E | −0.5177 | −0.1217 | 0.2747 | 0.058* | 0.35 |
H26F | −0.6122 | −0.0862 | 0.3084 | 0.058* | 0.35 |
C27U | −0.7648 (5) | 0.0248 (5) | 0.2334 (2) | 0.0380 (14) | 0.353 (4) |
H27D | −0.8223 | 0.0274 | 0.1970 | 0.057* | 0.35 |
H27E | −0.7363 | 0.1029 | 0.2435 | 0.057* | 0.35 |
H27F | −0.7965 | −0.0060 | 0.2650 | 0.057* | 0.35 |
C28 | −0.07196 (13) | 0.26874 (14) | 0.03214 (7) | 0.0237 (3) | |
C29 | −0.04331 (15) | 0.2709 (2) | −0.02972 (8) | 0.0416 (5) | |
H29A | −0.0930 | 0.3250 | −0.0552 | 0.062* | |
H29B | −0.0530 | 0.1934 | −0.0469 | 0.062* | |
H29C | 0.0340 | 0.2956 | −0.0258 | 0.062* | |
C30 | −0.05239 (16) | 0.39257 (18) | 0.05877 (10) | 0.0436 (5) | |
H30A | −0.1033 | 0.4469 | 0.0342 | 0.065* | |
H30B | 0.0246 | 0.4160 | 0.0604 | 0.065* | |
H30C | −0.0662 | 0.3925 | 0.0984 | 0.065* | |
C31 | 0.00802 (15) | 0.1819 (2) | 0.07142 (11) | 0.0510 (6) | |
H31A | 0.0852 | 0.2051 | 0.0735 | 0.077* | |
H31B | −0.0043 | 0.1043 | 0.0545 | 0.077* | |
H31C | −0.0065 | 0.1817 | 0.1109 | 0.077* | |
N1 | 0.80951 (15) | 0.51476 (16) | 0.18129 (7) | 0.0441 (4) | |
C32 | 0.74631 (15) | 0.51537 (15) | 0.13629 (8) | 0.0305 (4) | |
C33 | 0.66667 (17) | 0.51612 (17) | 0.07866 (8) | 0.0382 (4) | |
H33A | 0.6654 | 0.4398 | 0.0605 | 0.057* | |
H33B | 0.6897 | 0.5741 | 0.0533 | 0.057* | |
H33C | 0.5922 | 0.5350 | 0.0841 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0252 (2) | 0.0245 (2) | 0.0202 (2) | 0.00229 (16) | 0.00342 (16) | −0.00158 (15) |
F1 | 0.0531 (7) | 0.0334 (6) | 0.0302 (5) | 0.0000 (5) | −0.0011 (5) | −0.0093 (4) |
F2 | 0.0330 (6) | 0.0319 (6) | 0.0653 (8) | 0.0104 (5) | 0.0012 (5) | 0.0002 (5) |
F3 | 0.0264 (6) | 0.0448 (6) | 0.0673 (8) | 0.0082 (5) | 0.0093 (5) | −0.0077 (6) |
F4 | 0.0453 (6) | 0.0344 (6) | 0.0477 (6) | 0.0000 (5) | 0.0154 (5) | 0.0111 (5) |
F5 | 0.0692 (9) | 0.0462 (7) | 0.0367 (6) | 0.0069 (6) | −0.0134 (6) | −0.0190 (5) |
F6 | 0.0782 (9) | 0.0528 (7) | 0.0427 (7) | −0.0055 (6) | 0.0292 (6) | 0.0126 (6) |
O1 | 0.0192 (5) | 0.0231 (5) | 0.0156 (5) | −0.0019 (4) | 0.0029 (4) | 0.0019 (4) |
O2 | 0.0159 (5) | 0.0265 (5) | 0.0172 (5) | −0.0019 (4) | 0.0027 (4) | −0.0002 (4) |
O3 | 0.0165 (5) | 0.0248 (5) | 0.0149 (5) | −0.0034 (4) | 0.0030 (4) | 0.0006 (4) |
C1 | 0.0187 (7) | 0.0129 (6) | 0.0185 (7) | 0.0022 (5) | 0.0045 (6) | −0.0020 (5) |
C2 | 0.0175 (7) | 0.0161 (7) | 0.0172 (7) | 0.0015 (5) | 0.0028 (5) | −0.0015 (5) |
C3 | 0.0185 (7) | 0.0161 (7) | 0.0196 (7) | 0.0016 (5) | 0.0043 (6) | −0.0005 (5) |
C4 | 0.0236 (8) | 0.0214 (7) | 0.0180 (7) | 0.0024 (6) | 0.0044 (6) | 0.0019 (6) |
C5 | 0.0224 (8) | 0.0219 (7) | 0.0199 (7) | 0.0050 (6) | 0.0005 (6) | −0.0003 (6) |
C6 | 0.0163 (7) | 0.0242 (7) | 0.0228 (8) | 0.0004 (6) | 0.0017 (6) | −0.0019 (6) |
C7 | 0.0192 (7) | 0.0185 (7) | 0.0193 (7) | 0.0023 (5) | 0.0053 (6) | −0.0004 (5) |
C8 | 0.0179 (7) | 0.0163 (7) | 0.0165 (7) | 0.0004 (5) | 0.0049 (5) | −0.0021 (5) |
C9 | 0.0182 (7) | 0.0189 (7) | 0.0172 (7) | 0.0004 (5) | 0.0035 (6) | −0.0033 (5) |
C10 | 0.0190 (7) | 0.0236 (7) | 0.0215 (7) | −0.0048 (6) | 0.0077 (6) | −0.0036 (6) |
C11 | 0.0250 (8) | 0.0221 (7) | 0.0180 (7) | −0.0041 (6) | 0.0077 (6) | −0.0030 (6) |
C12 | 0.0215 (7) | 0.0230 (7) | 0.0149 (7) | −0.0024 (6) | 0.0031 (6) | −0.0009 (6) |
C13 | 0.0168 (7) | 0.0167 (7) | 0.0187 (7) | −0.0007 (5) | 0.0049 (5) | −0.0022 (5) |
C14 | 0.0178 (7) | 0.0147 (6) | 0.0175 (7) | −0.0004 (5) | 0.0050 (5) | −0.0013 (5) |
C15 | 0.0205 (7) | 0.0168 (7) | 0.0154 (7) | 0.0001 (5) | 0.0061 (6) | −0.0008 (5) |
C16 | 0.0178 (7) | 0.0212 (7) | 0.0188 (7) | −0.0006 (6) | 0.0022 (6) | −0.0012 (6) |
C17 | 0.0193 (7) | 0.0159 (7) | 0.0242 (7) | −0.0013 (5) | 0.0064 (6) | −0.0026 (6) |
C18 | 0.0220 (8) | 0.0179 (7) | 0.0198 (7) | −0.0014 (6) | 0.0081 (6) | 0.0004 (6) |
C19 | 0.0207 (7) | 0.0153 (7) | 0.0160 (7) | 0.0007 (5) | 0.0036 (6) | −0.0007 (5) |
C20 | 0.0238 (8) | 0.0357 (9) | 0.0200 (8) | 0.0020 (7) | −0.0035 (6) | 0.0038 (7) |
C21 | 0.0354 (10) | 0.0380 (9) | 0.0200 (8) | 0.0002 (8) | −0.0046 (7) | 0.0051 (7) |
C22 | 0.0257 (9) | 0.0637 (13) | 0.0356 (10) | 0.0118 (9) | −0.0038 (8) | 0.0088 (9) |
C23 | 0.0379 (10) | 0.0423 (10) | 0.0223 (8) | −0.0100 (8) | −0.0076 (7) | 0.0016 (7) |
C24 | 0.0416 (10) | 0.0391 (10) | 0.0210 (8) | −0.0191 (8) | 0.0124 (7) | −0.0008 (7) |
C25 | 0.0299 (15) | 0.0520 (19) | 0.0226 (13) | −0.0166 (15) | 0.0070 (11) | 0.0056 (12) |
C26 | 0.0408 (17) | 0.0370 (16) | 0.0327 (15) | −0.0028 (12) | 0.0112 (12) | 0.0135 (12) |
C27 | 0.0383 (16) | 0.0459 (19) | 0.0214 (13) | −0.0132 (14) | 0.0142 (11) | −0.0047 (12) |
C25U | 0.035 (3) | 0.031 (3) | 0.031 (3) | −0.009 (2) | 0.008 (2) | 0.004 (2) |
C26U | 0.040 (3) | 0.055 (4) | 0.021 (2) | −0.019 (3) | 0.007 (2) | 0.009 (2) |
C27U | 0.051 (3) | 0.043 (3) | 0.028 (3) | 0.008 (2) | 0.024 (2) | 0.004 (2) |
C28 | 0.0174 (7) | 0.0285 (8) | 0.0258 (8) | −0.0037 (6) | 0.0062 (6) | −0.0010 (6) |
C29 | 0.0240 (9) | 0.0685 (14) | 0.0360 (10) | −0.0106 (9) | 0.0144 (8) | −0.0092 (9) |
C30 | 0.0297 (10) | 0.0419 (11) | 0.0628 (13) | −0.0171 (8) | 0.0183 (9) | −0.0190 (10) |
C31 | 0.0189 (9) | 0.0645 (14) | 0.0711 (15) | 0.0061 (9) | 0.0128 (9) | 0.0321 (12) |
N1 | 0.0475 (10) | 0.0495 (10) | 0.0333 (9) | 0.0025 (8) | 0.0049 (8) | −0.0001 (7) |
C32 | 0.0332 (9) | 0.0293 (9) | 0.0318 (9) | 0.0012 (7) | 0.0134 (8) | 0.0011 (7) |
C33 | 0.0407 (11) | 0.0340 (10) | 0.0366 (10) | 0.0029 (8) | 0.0015 (8) | 0.0000 (8) |
Geometric parameters (Å, º) top
P1—F6 | 1.5842 (12) | C10—C11 | 1.404 (2) |
P1—F5 | 1.5861 (11) | C11—C12 | 1.411 (2) |
P1—F3 | 1.5916 (11) | C11—C24 | 1.531 (2) |
P1—F4 | 1.5993 (11) | C12—C13 | 1.376 (2) |
P1—F1 | 1.6037 (11) | C14—C15 | 1.400 (2) |
P1—F2 | 1.6055 (11) | C14—C19 | 1.403 (2) |
O1—C3 | 1.3780 (18) | C15—C16 | 1.376 (2) |
O1—C19 | 1.3818 (17) | C16—C17 | 1.412 (2) |
O2—C9 | 1.3794 (17) | C17—C18 | 1.405 (2) |
O2—C7 | 1.3797 (17) | C17—C28 | 1.536 (2) |
O3—C15 | 1.3806 (17) | C18—C19 | 1.377 (2) |
O3—C13 | 1.3821 (17) | C20—C21 | 1.530 (2) |
C1—C8 | 1.387 (2) | C20—C22 | 1.534 (2) |
C1—C2 | 1.392 (2) | C20—C23 | 1.538 (3) |
C1—C14 | 1.392 (2) | C24—C26U | 1.368 (5) |
C2—C3 | 1.402 (2) | C24—C25 | 1.468 (3) |
C2—C7 | 1.403 (2) | C24—C25U | 1.510 (5) |
C3—C4 | 1.380 (2) | C24—C27 | 1.524 (3) |
C4—C5 | 1.404 (2) | C24—C26 | 1.644 (3) |
C5—C6 | 1.412 (2) | C24—C27U | 1.732 (6) |
C5—C20 | 1.532 (2) | C28—C31 | 1.526 (2) |
C6—C7 | 1.372 (2) | C28—C30 | 1.529 (2) |
C8—C13 | 1.402 (2) | C28—C29 | 1.534 (2) |
C8—C9 | 1.403 (2) | N1—C32 | 1.139 (2) |
C9—C10 | 1.374 (2) | C32—C33 | 1.451 (3) |
| | | |
F6—P1—F5 | 91.27 (7) | C1—C14—C15 | 119.57 (13) |
F6—P1—F3 | 90.96 (7) | C1—C14—C19 | 119.80 (13) |
F5—P1—F3 | 90.33 (7) | C15—C14—C19 | 120.60 (13) |
F6—P1—F4 | 179.22 (7) | C16—C15—O3 | 120.09 (13) |
F5—P1—F4 | 89.42 (7) | C16—C15—C14 | 119.77 (13) |
F3—P1—F4 | 89.38 (7) | O3—C15—C14 | 120.11 (12) |
F6—P1—F1 | 89.40 (7) | C15—C16—C17 | 119.57 (13) |
F5—P1—F1 | 179.13 (7) | C18—C17—C16 | 120.58 (13) |
F3—P1—F1 | 90.21 (7) | C18—C17—C28 | 120.35 (13) |
F4—P1—F1 | 89.90 (6) | C16—C17—C28 | 119.05 (13) |
F6—P1—F2 | 90.09 (7) | C19—C18—C17 | 119.33 (13) |
F5—P1—F2 | 90.00 (7) | C18—C19—O1 | 119.87 (12) |
F3—P1—F2 | 178.90 (7) | C18—C19—C14 | 120.09 (13) |
F4—P1—F2 | 89.57 (6) | O1—C19—C14 | 120.02 (13) |
F1—P1—F2 | 89.45 (7) | C21—C20—C5 | 112.46 (14) |
C3—O1—C19 | 120.37 (11) | C21—C20—C22 | 108.04 (14) |
C9—O2—C7 | 120.32 (11) | C5—C20—C22 | 109.26 (14) |
C15—O3—C13 | 120.56 (11) | C21—C20—C23 | 109.01 (14) |
C8—C1—C2 | 120.13 (13) | C5—C20—C23 | 108.06 (13) |
C8—C1—C14 | 120.04 (13) | C22—C20—C23 | 110.00 (15) |
C2—C1—C14 | 119.78 (13) | C26U—C24—C25 | 126.4 (3) |
C1—C2—C3 | 119.85 (13) | C26U—C24—C25U | 117.8 (3) |
C1—C2—C7 | 119.67 (13) | C25—C24—C25U | 40.7 (2) |
C3—C2—C7 | 120.46 (13) | C26U—C24—C27 | 45.3 (3) |
O1—C3—C4 | 119.75 (13) | C25—C24—C27 | 112.8 (2) |
O1—C3—C2 | 120.15 (13) | C25U—C24—C27 | 140.3 (3) |
C4—C3—C2 | 120.09 (13) | C26U—C24—C11 | 118.0 (2) |
C3—C4—C5 | 119.26 (14) | C25—C24—C11 | 115.65 (16) |
C4—C5—C6 | 120.68 (13) | C25U—C24—C11 | 108.7 (2) |
C4—C5—C20 | 121.44 (14) | C27—C24—C11 | 110.45 (16) |
C6—C5—C20 | 117.86 (14) | C26U—C24—C26 | 59.7 (3) |
C7—C6—C5 | 119.54 (14) | C25—C24—C26 | 105.7 (2) |
C6—C7—O2 | 119.99 (13) | C25U—C24—C26 | 69.6 (3) |
C6—C7—C2 | 119.96 (13) | C27—C24—C26 | 104.9 (2) |
O2—C7—C2 | 120.02 (13) | C11—C24—C26 | 106.45 (15) |
C1—C8—C13 | 120.06 (13) | C26U—C24—C27U | 106.6 (3) |
C1—C8—C9 | 119.59 (13) | C25—C24—C27U | 61.3 (3) |
C13—C8—C9 | 120.35 (13) | C25U—C24—C27U | 102.0 (3) |
C10—C9—O2 | 119.89 (13) | C27—C24—C27U | 64.1 (2) |
C10—C9—C8 | 119.85 (13) | C11—C24—C27U | 101.1 (2) |
O2—C9—C8 | 120.24 (12) | C26—C24—C27U | 152.5 (2) |
C9—C10—C11 | 119.68 (13) | C31—C28—C30 | 109.66 (16) |
C10—C11—C12 | 120.80 (13) | C31—C28—C29 | 108.20 (15) |
C10—C11—C24 | 119.75 (14) | C30—C28—C29 | 107.94 (15) |
C12—C11—C24 | 119.45 (14) | C31—C28—C17 | 111.09 (13) |
C13—C12—C11 | 118.92 (13) | C30—C28—C17 | 107.81 (13) |
C12—C13—O3 | 119.98 (13) | C29—C28—C17 | 112.08 (13) |
C12—C13—C8 | 120.37 (13) | N1—C32—C33 | 179.44 (19) |
O3—C13—C8 | 119.64 (12) | | |
(12) Bis(2,6,10-tri-
tert-butyl-4,8,12-trioxa-4,8,12,12
c-tetrahydro-
dibenzo[cd,mn]pyrenium) tetradecachlorohexamolybdate
top
Crystal data top
C31H33O3·Cl7Mo3 | Z = 4 |
Mr = 989.54 | F(000) = 1952 |
Monoclinic, P21/n | Dx = 1.877 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 17.157 (3) Å | µ = 1.62 mm−1 |
b = 11.130 (2) Å | T = 120 K |
c = 18.456 (4) Å | Cube, orange |
β = 96.40 (3)° | 0.28 × 0.20 × 0.20 mm |
V = 3502.4 (12) Å3 | |
Data collection top
Siemens SMART CCD diffractometer | 7149 independent reflections |
Radiation source: fine-focus sealed tube | 6258 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scan, frame data integration | θmax = 26.4°, θmin = 1.5° |
Absorption correction: empirical (using intensity measurements) | h = −21→21 |
Tmin = 0.704, Tmax = 0.886 | k = −13→13 |
36072 measured reflections | l = −23→23 |
Refinement top
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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Calculated w = 1/[σ2(Fo2) + (0.0303P)2 + 1.6569P] where P = (Fo2 + 2Fc2)/3 |
7149 reflections | (Δ/σ)max = 0.005 |
397 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −1.31 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Mo1 | 0.950784 (10) | 0.876155 (17) | 0.043899 (10) | 0.01156 (5) | |
Mo2 | 1.014830 (10) | 1.079316 (17) | 0.088032 (10) | 0.01214 (5) | |
Mo3 | 1.095215 (10) | 0.923207 (17) | 0.021136 (10) | 0.01187 (5) | |
Cl1 | 0.88433 (3) | 0.71653 (5) | 0.10371 (3) | 0.02044 (12) | |
Cl2 | 1.03377 (4) | 1.17836 (6) | 0.20545 (3) | 0.02654 (14) | |
Cl3 | 1.22017 (3) | 0.81908 (5) | 0.04631 (3) | 0.02215 (13) | |
Cl4 | 0.87735 (3) | 1.03036 (5) | 0.10448 (3) | 0.01702 (12) | |
Cl5 | 1.15006 (3) | 1.12096 (5) | 0.06237 (3) | 0.01617 (11) | |
Cl6 | 1.02882 (3) | 0.73467 (5) | −0.02202 (3) | 0.01627 (11) | |
Cl7 | 1.05821 (3) | 0.88635 (5) | 0.14517 (3) | 0.01713 (11) | |
O1 | 0.45707 (8) | 0.82772 (14) | −0.15806 (8) | 0.0135 (3) | |
O2 | 0.31766 (8) | 1.08819 (14) | −0.00779 (8) | 0.0139 (3) | |
O3 | 0.49862 (8) | 0.79292 (14) | 0.10404 (8) | 0.0143 (3) | |
C1 | 0.42274 (12) | 0.90108 (19) | −0.02062 (12) | 0.0116 (4) | |
C2 | 0.38625 (12) | 0.9570 (2) | −0.08306 (12) | 0.0126 (4) | |
C3 | 0.40530 (12) | 0.92167 (19) | −0.15203 (12) | 0.0130 (4) | |
C4 | 0.37376 (12) | 0.9821 (2) | −0.21344 (11) | 0.0140 (4) | |
H4 | 0.3863 | 0.9595 | −0.2592 | 0.017* | |
C5 | 0.32230 (12) | 1.0787 (2) | −0.20608 (12) | 0.0136 (4) | |
C6 | 0.30081 (12) | 1.1120 (2) | −0.13717 (12) | 0.0147 (4) | |
H6 | 0.2648 | 1.1734 | −0.1331 | 0.018* | |
C7 | 0.33425 (12) | 1.0517 (2) | −0.07596 (12) | 0.0132 (4) | |
C8 | 0.40717 (12) | 0.93901 (19) | 0.04778 (12) | 0.0121 (4) | |
C9 | 0.35416 (12) | 1.0337 (2) | 0.05407 (12) | 0.0130 (4) | |
C10 | 0.33960 (12) | 1.07279 (19) | 0.12195 (12) | 0.0137 (4) | |
H10 | 0.3059 | 1.1371 | 0.1264 | 0.016* | |
C11 | 0.37588 (12) | 1.01525 (19) | 0.18422 (12) | 0.0128 (4) | |
C12 | 0.42924 (12) | 0.9201 (2) | 0.17862 (12) | 0.0137 (4) | |
H12 | 0.4534 | 0.8827 | 0.2203 | 0.016* | |
C13 | 0.44492 (12) | 0.88392 (19) | 0.11086 (12) | 0.0124 (4) | |
C14 | 0.47708 (12) | 0.80968 (19) | −0.02700 (11) | 0.0125 (4) | |
C15 | 0.51501 (12) | 0.75612 (19) | 0.03610 (11) | 0.0123 (4) | |
C16 | 0.56837 (12) | 0.6654 (2) | 0.02997 (12) | 0.0138 (4) | |
H16 | 0.5941 | 0.6300 | 0.0716 | 0.017* | |
C17 | 0.58391 (12) | 0.62647 (19) | −0.03938 (12) | 0.0134 (4) | |
C18 | 0.54567 (12) | 0.6798 (2) | −0.10273 (12) | 0.0137 (4) | |
H18 | 0.5557 | 0.6531 | −0.1485 | 0.016* | |
C19 | 0.49324 (12) | 0.7719 (2) | −0.09639 (11) | 0.0127 (4) | |
C20 | 0.28787 (13) | 1.1522 (2) | −0.27219 (12) | 0.0168 (5) | |
C21 | 0.19862 (14) | 1.1307 (2) | −0.28355 (13) | 0.0215 (5) | |
H21A | 0.1763 | 1.1509 | −0.2397 | 0.032* | |
H21B | 0.1885 | 1.0476 | −0.2951 | 0.032* | |
H21C | 0.1756 | 1.1800 | −0.3229 | 0.032* | |
C22 | 0.32445 (14) | 1.1189 (2) | −0.34166 (13) | 0.0232 (5) | |
H22A | 0.3800 | 1.1323 | −0.3341 | 0.035* | |
H22B | 0.3018 | 1.1677 | −0.3814 | 0.035* | |
H22C | 0.3144 | 1.0357 | −0.3529 | 0.035* | |
C23 | 0.30369 (15) | 1.2866 (2) | −0.25642 (13) | 0.0236 (5) | |
H23A | 0.3592 | 1.3005 | −0.2491 | 0.035* | |
H23B | 0.2807 | 1.3095 | −0.2134 | 0.035* | |
H23C | 0.2810 | 1.3336 | −0.2970 | 0.035* | |
C24 | 0.35515 (13) | 1.0489 (2) | 0.26010 (12) | 0.0171 (5) | |
C25 | 0.30681 (14) | 1.1646 (2) | 0.25967 (13) | 0.0229 (5) | |
H25A | 0.2602 | 1.1562 | 0.2261 | 0.034* | |
H25B | 0.3374 | 1.2307 | 0.2450 | 0.034* | |
H25C | 0.2925 | 1.1794 | 0.3077 | 0.034* | |
C26 | 0.43001 (16) | 1.0650 (3) | 0.31308 (14) | 0.0298 (6) | |
H26A | 0.4161 | 1.0855 | 0.3605 | 0.045* | |
H26B | 0.4613 | 1.1281 | 0.2958 | 0.045* | |
H26C | 0.4594 | 0.9914 | 0.3160 | 0.045* | |
C27 | 0.30638 (18) | 0.9441 (3) | 0.28503 (16) | 0.0346 (7) | |
H27A | 0.2600 | 0.9342 | 0.2514 | 0.052* | |
H27B | 0.2918 | 0.9609 | 0.3327 | 0.052* | |
H27C | 0.3369 | 0.8716 | 0.2866 | 0.052* | |
C28 | 0.64667 (12) | 0.5300 (2) | −0.04476 (12) | 0.0143 (4) | |
C29 | 0.63263 (14) | 0.4595 (2) | −0.11678 (13) | 0.0203 (5) | |
H29A | 0.6328 | 0.5140 | −0.1571 | 0.031* | |
H29B | 0.5828 | 0.4195 | −0.1195 | 0.031* | |
H29C | 0.6735 | 0.4010 | −0.1187 | 0.031* | |
C30 | 0.72640 (14) | 0.5947 (2) | −0.03938 (14) | 0.0228 (5) | |
H30A | 0.7344 | 0.6384 | 0.0057 | 0.034* | |
H30B | 0.7270 | 0.6495 | −0.0795 | 0.034* | |
H30C | 0.7675 | 0.5366 | −0.0410 | 0.034* | |
C31 | 0.64836 (14) | 0.4411 (2) | 0.01860 (14) | 0.0219 (5) | |
H31A | 0.6552 | 0.4841 | 0.0639 | 0.033* | |
H31B | 0.6911 | 0.3860 | 0.0166 | 0.033* | |
H31C | 0.5999 | 0.3973 | 0.0150 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Mo1 | 0.01039 (9) | 0.01106 (10) | 0.01335 (10) | −0.00042 (7) | 0.00189 (7) | −0.00083 (7) |
Mo2 | 0.01238 (9) | 0.01202 (10) | 0.01198 (10) | −0.00028 (7) | 0.00120 (7) | −0.00290 (7) |
Mo3 | 0.00936 (9) | 0.01110 (10) | 0.01507 (10) | 0.00076 (7) | 0.00105 (7) | −0.00121 (7) |
Cl1 | 0.0187 (3) | 0.0178 (3) | 0.0252 (3) | −0.0031 (2) | 0.0044 (2) | 0.0046 (2) |
Cl2 | 0.0354 (3) | 0.0265 (3) | 0.0173 (3) | −0.0032 (3) | 0.0011 (2) | −0.0103 (2) |
Cl3 | 0.0127 (2) | 0.0180 (3) | 0.0352 (3) | 0.0039 (2) | 0.0003 (2) | 0.0011 (2) |
Cl4 | 0.0158 (3) | 0.0175 (3) | 0.0190 (3) | 0.0003 (2) | 0.0074 (2) | −0.0028 (2) |
Cl5 | 0.0120 (2) | 0.0156 (3) | 0.0203 (3) | −0.00195 (19) | −0.0012 (2) | −0.0021 (2) |
Cl6 | 0.0158 (2) | 0.0117 (3) | 0.0215 (3) | 0.0010 (2) | 0.0030 (2) | −0.0031 (2) |
Cl7 | 0.0182 (3) | 0.0174 (3) | 0.0150 (3) | 0.0000 (2) | −0.0013 (2) | 0.0017 (2) |
O1 | 0.0156 (7) | 0.0132 (8) | 0.0118 (7) | 0.0033 (6) | 0.0023 (6) | 0.0004 (6) |
O2 | 0.0133 (7) | 0.0150 (8) | 0.0137 (8) | 0.0036 (6) | 0.0032 (6) | 0.0012 (6) |
O3 | 0.0161 (7) | 0.0145 (8) | 0.0126 (7) | 0.0042 (6) | 0.0032 (6) | 0.0008 (6) |
C1 | 0.0097 (9) | 0.0091 (10) | 0.0162 (11) | −0.0030 (8) | 0.0027 (8) | −0.0001 (8) |
C2 | 0.0105 (10) | 0.0121 (11) | 0.0154 (11) | −0.0002 (8) | 0.0021 (8) | 0.0020 (8) |
C3 | 0.0103 (10) | 0.0118 (11) | 0.0169 (11) | −0.0009 (8) | 0.0022 (8) | 0.0000 (9) |
C4 | 0.0139 (10) | 0.0162 (12) | 0.0121 (10) | −0.0013 (9) | 0.0028 (8) | −0.0003 (9) |
C5 | 0.0114 (10) | 0.0131 (11) | 0.0161 (11) | −0.0019 (8) | 0.0012 (8) | 0.0023 (9) |
C6 | 0.0125 (10) | 0.0127 (11) | 0.0190 (11) | 0.0019 (8) | 0.0028 (9) | 0.0015 (9) |
C7 | 0.0110 (10) | 0.0143 (11) | 0.0144 (11) | −0.0019 (8) | 0.0027 (8) | −0.0011 (9) |
C8 | 0.0112 (10) | 0.0113 (11) | 0.0143 (11) | −0.0015 (8) | 0.0033 (8) | 0.0002 (8) |
C9 | 0.0113 (10) | 0.0130 (11) | 0.0146 (11) | −0.0015 (8) | 0.0016 (8) | 0.0016 (9) |
C10 | 0.0103 (10) | 0.0127 (11) | 0.0184 (11) | −0.0018 (8) | 0.0035 (8) | −0.0027 (9) |
C11 | 0.0115 (10) | 0.0123 (11) | 0.0154 (11) | −0.0053 (8) | 0.0048 (8) | −0.0032 (9) |
C12 | 0.0147 (10) | 0.0134 (11) | 0.0130 (11) | −0.0020 (8) | 0.0013 (8) | 0.0022 (9) |
C13 | 0.0115 (10) | 0.0091 (11) | 0.0171 (11) | 0.0007 (8) | 0.0034 (8) | 0.0016 (8) |
C14 | 0.0119 (10) | 0.0103 (10) | 0.0159 (11) | −0.0012 (8) | 0.0039 (8) | −0.0013 (8) |
C15 | 0.0121 (10) | 0.0118 (11) | 0.0136 (10) | −0.0010 (8) | 0.0040 (8) | −0.0012 (8) |
C16 | 0.0146 (10) | 0.0127 (11) | 0.0139 (10) | 0.0010 (8) | 0.0004 (8) | 0.0020 (9) |
C17 | 0.0114 (10) | 0.0105 (11) | 0.0189 (11) | −0.0021 (8) | 0.0042 (8) | −0.0003 (9) |
C18 | 0.0141 (10) | 0.0135 (11) | 0.0142 (10) | −0.0017 (8) | 0.0043 (8) | −0.0013 (9) |
C19 | 0.0112 (10) | 0.0123 (11) | 0.0149 (11) | −0.0013 (8) | 0.0034 (8) | 0.0027 (8) |
C20 | 0.0176 (11) | 0.0172 (12) | 0.0156 (11) | 0.0029 (9) | 0.0016 (9) | 0.0040 (9) |
C21 | 0.0189 (11) | 0.0254 (13) | 0.0196 (12) | 0.0044 (10) | −0.0012 (9) | 0.0028 (10) |
C22 | 0.0258 (13) | 0.0279 (14) | 0.0164 (12) | 0.0089 (10) | 0.0045 (10) | 0.0060 (10) |
C23 | 0.0294 (13) | 0.0188 (13) | 0.0230 (13) | 0.0021 (10) | 0.0045 (10) | 0.0064 (10) |
C24 | 0.0198 (11) | 0.0175 (12) | 0.0148 (11) | 0.0011 (9) | 0.0057 (9) | −0.0022 (9) |
C25 | 0.0251 (12) | 0.0258 (14) | 0.0183 (12) | 0.0067 (10) | 0.0046 (10) | −0.0060 (10) |
C26 | 0.0329 (14) | 0.0376 (16) | 0.0172 (12) | 0.0143 (12) | −0.0046 (11) | −0.0106 (11) |
C27 | 0.0465 (17) | 0.0268 (15) | 0.0362 (16) | −0.0020 (12) | 0.0301 (13) | 0.0022 (12) |
C28 | 0.0131 (10) | 0.0135 (11) | 0.0163 (11) | 0.0019 (9) | 0.0023 (8) | −0.0015 (9) |
C29 | 0.0212 (11) | 0.0178 (12) | 0.0220 (12) | 0.0061 (10) | 0.0023 (9) | −0.0040 (10) |
C30 | 0.0147 (11) | 0.0234 (13) | 0.0313 (14) | −0.0009 (10) | 0.0064 (10) | −0.0058 (11) |
C31 | 0.0251 (12) | 0.0162 (12) | 0.0255 (13) | 0.0073 (10) | 0.0073 (10) | 0.0025 (10) |
Geometric parameters (Å, º) top
Mo1—Cl1 | 2.4404 (7) | C1—C8 | 1.385 (3) |
Mo1—Cl5i | 2.4667 (10) | C1—C14 | 1.394 (3) |
Mo1—Cl4 | 2.4692 (7) | C1—C2 | 1.395 (3) |
Mo1—Cl6 | 2.4729 (7) | C2—C7 | 1.396 (3) |
Mo1—Cl7 | 2.4770 (10) | C2—C3 | 1.405 (3) |
Mo1—Mo2 | 2.6047 (5) | C3—C4 | 1.376 (3) |
Mo1—Mo3 | 2.6121 (6) | C4—C5 | 1.407 (3) |
Mo1—Mo3i | 2.6152 (5) | C5—C6 | 1.413 (3) |
Mo1—Mo2i | 2.6159 (6) | C5—C20 | 1.532 (3) |
Mo2—Cl2 | 2.4207 (7) | C6—C7 | 1.383 (3) |
Mo2—Cl5 | 2.4631 (8) | C8—C9 | 1.405 (3) |
Mo2—Cl7 | 2.4705 (7) | C8—C13 | 1.408 (3) |
Mo2—Cl4 | 2.4724 (7) | C9—C10 | 1.375 (3) |
Mo2—Cl6i | 2.4756 (7) | C10—C11 | 1.400 (3) |
Mo2—Mo3i | 2.6033 (9) | C11—C12 | 1.411 (3) |
Mo2—Mo3 | 2.6124 (5) | C11—C24 | 1.529 (3) |
Mo2—Mo1i | 2.6159 (6) | C12—C13 | 1.369 (3) |
Mo3—Cl3 | 2.4358 (7) | C14—C15 | 1.402 (3) |
Mo3—Cl4i | 2.4712 (7) | C14—C19 | 1.405 (3) |
Mo3—Cl6 | 2.4765 (7) | C15—C16 | 1.376 (3) |
Mo3—Cl7 | 2.4770 (8) | C16—C17 | 1.405 (3) |
Mo3—Cl5 | 2.4797 (7) | C17—C18 | 1.407 (3) |
Mo3—Mo2i | 2.6032 (9) | C17—C28 | 1.532 (3) |
Mo3—Mo1i | 2.6152 (5) | C18—C19 | 1.377 (3) |
Cl4—Mo3i | 2.4713 (7) | C20—C22 | 1.535 (3) |
Cl5—Mo1i | 2.4668 (10) | C20—C21 | 1.541 (3) |
Cl6—Mo2i | 2.4755 (7) | C20—C23 | 1.542 (3) |
O1—C19 | 1.382 (3) | C24—C25 | 1.532 (3) |
O1—C3 | 1.385 (3) | C24—C26 | 1.536 (3) |
O2—C9 | 1.380 (3) | C24—C27 | 1.535 (3) |
O2—C7 | 1.382 (3) | C28—C31 | 1.530 (3) |
O3—C15 | 1.377 (2) | C28—C30 | 1.540 (3) |
O3—C13 | 1.384 (2) | C28—C29 | 1.539 (3) |
| | | |
Cl1—Mo1—Cl5i | 92.72 (2) | Cl3—Mo3—Mo2 | 136.56 (2) |
Cl1—Mo1—Cl4 | 90.77 (3) | Cl4i—Mo3—Mo2 | 118.04 (2) |
Cl5i—Mo1—Cl4 | 90.17 (2) | Cl6—Mo3—Mo2 | 117.865 (19) |
Cl1—Mo1—Cl6 | 93.72 (3) | Cl7—Mo3—Mo2 | 58.01 (2) |
Cl5i—Mo1—Cl6 | 89.28 (2) | Cl5—Mo3—Mo2 | 57.785 (18) |
Cl4—Mo1—Cl6 | 175.499 (19) | Mo2i—Mo3—Mo2 | 89.853 (15) |
Cl1—Mo1—Cl7 | 92.17 (2) | Mo1—Mo3—Mo2 | 59.808 (16) |
Cl5i—Mo1—Cl7 | 175.10 (2) | Cl3—Mo3—Mo1i | 135.07 (2) |
Cl4—Mo1—Cl7 | 90.05 (2) | Cl4i—Mo3—Mo1i | 58.001 (17) |
Cl6—Mo1—Cl7 | 90.13 (2) | Cl6—Mo3—Mo1i | 118.13 (2) |
Cl1—Mo1—Mo2 | 133.837 (19) | Cl7—Mo3—Mo1i | 118.052 (17) |
Cl5i—Mo1—Mo2 | 118.124 (18) | Cl5—Mo3—Mo1i | 57.84 (2) |
Cl4—Mo1—Mo2 | 58.250 (18) | Mo2i—Mo3—Mo1i | 59.883 (12) |
Cl6—Mo1—Mo2 | 118.294 (19) | Mo1—Mo3—Mo1i | 90.106 (16) |
Cl7—Mo1—Mo2 | 58.113 (16) | Mo2—Mo3—Mo1i | 60.054 (15) |
Cl1—Mo1—Mo3 | 135.900 (19) | Mo1—Cl4—Mo3i | 63.92 (2) |
Cl5i—Mo1—Mo3 | 117.61 (2) | Mo1—Cl4—Mo2 | 63.62 (2) |
Cl4—Mo1—Mo3 | 118.33 (2) | Mo3i—Cl4—Mo2 | 63.55 (3) |
Cl6—Mo1—Mo3 | 58.21 (2) | Mo2—Cl5—Mo1i | 64.10 (2) |
Cl7—Mo1—Mo3 | 58.18 (2) | Mo2—Cl5—Mo3 | 63.811 (16) |
Mo2—Mo1—Mo3 | 60.102 (11) | Mo1i—Cl5—Mo3 | 63.834 (16) |
Cl1—Mo1—Mo3i | 134.185 (19) | Mo1—Cl6—Mo2i | 63.826 (19) |
Cl5i—Mo1—Mo3i | 58.324 (16) | Mo1—Cl6—Mo3 | 63.709 (19) |
Cl4—Mo1—Mo3i | 58.078 (19) | Mo2i—Cl6—Mo3 | 63.43 (2) |
Cl6—Mo1—Mo3i | 118.04 (2) | Mo2—Cl7—Mo3 | 63.744 (17) |
Cl7—Mo1—Mo3i | 117.925 (19) | Mo2—Cl7—Mo1 | 63.534 (17) |
Mo2—Mo1—Mo3i | 59.83 (2) | Mo3—Cl7—Mo1 | 63.64 (2) |
Mo3—Mo1—Mo3i | 89.892 (16) | C19—O1—C3 | 120.45 (16) |
Cl1—Mo1—Mo2i | 136.404 (19) | C9—O2—C7 | 120.23 (17) |
Cl5i—Mo1—Mo2i | 57.89 (2) | C15—O3—C13 | 120.38 (17) |
Cl4—Mo1—Mo2i | 117.98 (2) | C8—C1—C14 | 119.9 (2) |
Cl6—Mo1—Mo2i | 58.14 (2) | C8—C1—C2 | 120.2 (2) |
Cl7—Mo1—Mo2i | 117.88 (2) | C14—C1—C2 | 119.9 (2) |
Mo2—Mo1—Mo2i | 89.745 (14) | C7—C2—C1 | 119.4 (2) |
Mo3—Mo1—Mo2i | 59.73 (3) | C7—C2—C3 | 120.8 (2) |
Mo3i—Mo1—Mo2i | 59.919 (12) | C1—C2—C3 | 119.7 (2) |
Cl2—Mo2—Cl5 | 92.93 (3) | C4—C3—O1 | 120.01 (19) |
Cl2—Mo2—Cl7 | 90.56 (3) | C4—C3—C2 | 120.0 (2) |
Cl5—Mo2—Cl7 | 90.01 (2) | O1—C3—C2 | 120.01 (19) |
Cl2—Mo2—Cl4 | 91.44 (3) | C3—C4—C5 | 119.2 (2) |
Cl5—Mo2—Cl4 | 175.623 (19) | C4—C5—C6 | 121.1 (2) |
Cl7—Mo2—Cl4 | 90.12 (2) | C4—C5—C20 | 121.44 (19) |
Cl2—Mo2—Cl6i | 93.60 (3) | C6—C5—C20 | 117.42 (19) |
Cl5—Mo2—Cl6i | 89.30 (2) | C7—C6—C5 | 118.8 (2) |
Cl7—Mo2—Cl6i | 175.811 (19) | O2—C7—C6 | 119.49 (19) |
Cl4—Mo2—Cl6i | 90.25 (2) | O2—C7—C2 | 120.41 (19) |
Cl2—Mo2—Mo3i | 135.33 (2) | C6—C7—C2 | 120.1 (2) |
Cl5—Mo2—Mo3i | 118.07 (2) | C1—C8—C9 | 119.8 (2) |
Cl7—Mo2—Mo3i | 118.618 (18) | C1—C8—C13 | 120.2 (2) |
Cl4—Mo2—Mo3i | 58.20 (2) | C9—C8—C13 | 120.04 (19) |
Cl6i—Mo2—Mo3i | 58.302 (17) | C10—C9—O2 | 120.18 (19) |
Cl2—Mo2—Mo1 | 133.25 (2) | C10—C9—C8 | 119.8 (2) |
Cl5—Mo2—Mo1 | 118.477 (17) | O2—C9—C8 | 119.97 (19) |
Cl7—Mo2—Mo1 | 58.35 (2) | C9—C10—C11 | 119.6 (2) |
Cl4—Mo2—Mo1 | 58.132 (16) | C10—C11—C12 | 121.06 (19) |
Cl6i—Mo2—Mo1 | 118.57 (2) | C10—C11—C24 | 120.83 (19) |
Mo3i—Mo2—Mo1 | 60.284 (11) | C12—C11—C24 | 118.01 (19) |
Cl2—Mo2—Mo3 | 134.48 (2) | C13—C12—C11 | 118.9 (2) |
Cl5—Mo2—Mo3 | 58.40 (2) | C12—C13—O3 | 119.94 (19) |
Cl7—Mo2—Mo3 | 58.249 (18) | C12—C13—C8 | 120.53 (19) |
Cl4—Mo2—Mo3 | 118.20 (2) | O3—C13—C8 | 119.53 (19) |
Cl6i—Mo2—Mo3 | 118.05 (2) | C1—C14—C15 | 119.54 (19) |
Mo3i—Mo2—Mo3 | 90.145 (15) | C1—C14—C19 | 119.8 (2) |
Mo1—Mo2—Mo3 | 60.090 (14) | C15—C14—C19 | 120.62 (19) |
Cl2—Mo2—Mo1i | 136.49 (2) | C16—C15—O3 | 119.88 (19) |
Cl5—Mo2—Mo1i | 58.02 (3) | C16—C15—C14 | 119.67 (19) |
Cl7—Mo2—Mo1i | 118.266 (17) | O3—C15—C14 | 120.44 (18) |
Cl4—Mo2—Mo1i | 118.25 (3) | C15—C16—C17 | 119.8 (2) |
Cl6i—Mo2—Mo1i | 58.037 (16) | C16—C17—C18 | 120.6 (2) |
Mo3i—Mo2—Mo1i | 60.061 (18) | C16—C17—C28 | 118.79 (19) |
Mo1—Mo2—Mo1i | 90.254 (15) | C18—C17—C28 | 120.54 (19) |
Mo3—Mo2—Mo1i | 60.026 (17) | C19—C18—C17 | 119.5 (2) |
Cl3—Mo3—Cl4i | 91.30 (3) | C18—C19—O1 | 120.16 (19) |
Cl3—Mo3—Cl6 | 91.24 (3) | C18—C19—C14 | 119.8 (2) |
Cl4i—Mo3—Cl6 | 90.25 (2) | O1—C19—C14 | 120.00 (19) |
Cl3—Mo3—Cl7 | 93.20 (3) | C5—C20—C22 | 112.26 (18) |
Cl4i—Mo3—Cl7 | 175.481 (19) | C5—C20—C21 | 108.31 (18) |
Cl6—Mo3—Cl7 | 90.05 (2) | C22—C20—C21 | 109.96 (19) |
Cl3—Mo3—Cl5 | 93.90 (2) | C5—C20—C23 | 108.90 (19) |
Cl4i—Mo3—Cl5 | 89.82 (2) | C22—C20—C23 | 108.21 (19) |
Cl6—Mo3—Cl5 | 174.856 (18) | C21—C20—C23 | 109.15 (19) |
Cl7—Mo3—Cl5 | 89.48 (2) | C11—C24—C25 | 112.46 (19) |
Cl3—Mo3—Mo2i | 133.59 (2) | C11—C24—C26 | 110.38 (18) |
Cl4i—Mo3—Mo2i | 58.24 (2) | C25—C24—C26 | 108.61 (19) |
Cl6—Mo3—Mo2i | 58.267 (17) | C11—C24—C27 | 106.19 (19) |
Cl7—Mo3—Mo2i | 118.36 (2) | C25—C24—C27 | 109.1 (2) |
Cl5—Mo3—Mo2i | 117.694 (17) | C26—C24—C27 | 110.1 (2) |
Cl3—Mo3—Mo1 | 134.789 (19) | C31—C28—C17 | 110.95 (18) |
Cl4i—Mo3—Mo1 | 118.43 (3) | C31—C28—C30 | 108.21 (19) |
Cl6—Mo3—Mo1 | 58.078 (16) | C17—C28—C30 | 107.06 (18) |
Cl7—Mo3—Mo1 | 58.18 (3) | C31—C28—C29 | 108.57 (19) |
Cl5—Mo3—Mo1 | 117.576 (17) | C17—C28—C29 | 111.69 (18) |
Mo2i—Mo3—Mo1 | 60.21 (2) | C30—C28—C29 | 110.29 (19) |
Symmetry code: (i) −x+2, −y+2, −z. |
(6160K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.752 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.26 mm−1 |
a = 12.964 (2) Å | T = 160 K |
c = 16.813 (3) Å | Prism, orange |
V = 2447.3 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 425 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8102 measured reflections | k = −15→16 |
561 independent reflections | l = −21→21 |
Refinement top
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
561 reflections | (Δ/σ)max = −0.007 |
47 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0292 (3) | |
F1 | 0.04964 (11) | 0.11613 (9) | 0.05494 (6) | 0.0436 (4) | |
O1 | 0.78529 (13) | 0.0000 | 0.2500 | 0.0366 (5) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0262 (9) | |
C2 | 1.0000 | 0.1072 (2) | 0.2500 | 0.0293 (6) | |
C3 | 0.8916 (2) | 0.1065 (2) | 0.25166 (9) | 0.0317 (4) | |
C4 | 0.8909 (2) | 0.2123 (2) | 0.25376 (10) | 0.0410 (5) | |
H4 | 0.8199 | 0.2136 | 0.2576 | 0.049* | |
C5 | 1.0000 | 0.3171 (2) | 0.2500 | 0.0439 (8) | |
H5 | 1.0000 | 0.3888 | 0.2500 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0277 (4) | 0.0277 (4) | 0.0323 (6) | 0.0138 (2) | 0.000 | 0.000 |
F1 | 0.0444 (7) | 0.0351 (7) | 0.0492 (7) | 0.0183 (6) | −0.0053 (5) | −0.0117 (5) |
O1 | 0.0324 (7) | 0.0458 (11) | 0.0360 (10) | 0.0229 (6) | 0.0012 (4) | 0.0025 (9) |
C1 | 0.0296 (13) | 0.0296 (13) | 0.020 (2) | 0.0148 (7) | 0.000 | 0.000 |
C2 | 0.0348 (14) | 0.0317 (10) | 0.0226 (11) | 0.0174 (7) | 0.0004 (10) | 0.0002 (5) |
C3 | 0.0374 (11) | 0.0357 (11) | 0.0249 (8) | 0.0204 (9) | 0.0006 (7) | 0.0007 (7) |
C4 | 0.0561 (13) | 0.0514 (13) | 0.0312 (10) | 0.0387 (11) | −0.0043 (9) | −0.0037 (9) |
C5 | 0.071 (2) | 0.0389 (11) | 0.0324 (14) | 0.0357 (11) | −0.0084 (14) | −0.0042 (7) |
Geometric parameters (Å, º) top
P1—F1i | 1.6017 (10) | C1—C2vii | 1.390 (3) |
P1—F1 | 1.6017 (10) | C1—C2 | 1.390 (3) |
P1—F1ii | 1.6017 (10) | C1—C2viii | 1.390 (3) |
P1—F1iii | 1.6017 (10) | C2—C3ix | 1.401 (2) |
P1—F1iv | 1.6017 (10) | C2—C3 | 1.401 (2) |
P1—F1v | 1.6017 (10) | C3—C4 | 1.378 (3) |
O1—C3 | 1.380 (2) | C4—C5 | 1.389 (2) |
O1—C3vi | 1.380 (2) | C5—C4ix | 1.389 (2) |
| | | |
F1i—P1—F1 | 180.0 | F1iv—P1—F1v | 89.94 (6) |
F1i—P1—F1ii | 89.94 (6) | C3—O1—C3vi | 120.2 (2) |
F1—P1—F1ii | 90.06 (6) | C2vii—C1—C2 | 120.0 |
F1i—P1—F1iii | 90.06 (6) | C2vii—C1—C2viii | 120.0 |
F1—P1—F1iii | 89.94 (6) | C2—C1—C2viii | 120.0 |
F1ii—P1—F1iii | 89.94 (6) | C1—C2—C3ix | 119.65 (13) |
F1i—P1—F1iv | 89.94 (6) | C1—C2—C3 | 119.65 (13) |
F1—P1—F1iv | 90.06 (6) | C3ix—C2—C3 | 120.7 (3) |
F1ii—P1—F1iv | 90.06 (6) | O1—C3—C4 | 119.7 (2) |
F1iii—P1—F1iv | 180.0 | O1—C3—C2 | 120.2 (2) |
F1i—P1—F1v | 90.06 (6) | C4—C3—C2 | 120.0 (2) |
F1—P1—F1v | 89.94 (6) | C3—C4—C5 | 117.5 (2) |
F1ii—P1—F1v | 180.0 | C4—C5—C4ix | 124.1 (3) |
F1iii—P1—F1v | 90.06 (6) | | |
Symmetry codes: (i) −x, −y, −z; (ii) −y, x−y, z; (iii) x−y, x, −z; (iv) −x+y, −x, z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6198K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.740 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 12.997 (2) Å | T = 198 K |
c = 16.843 (3) Å | Prism, orange |
V = 2464.0 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 397 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8165 measured reflections | k = −16→15 |
566 independent reflections | l = −21→21 |
Refinement top
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
566 reflections | (Δ/σ)max = 0.011 |
47 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0373 (4) | |
F1 | 0.04949 (12) | 0.11560 (11) | 0.05468 (7) | 0.0551 (5) | |
O1 | 0.7863 (2) | 0.0000 | 0.2500 | 0.0461 (6) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0333 (10) | |
C2 | 1.0000 | 0.1068 (2) | 0.2500 | 0.0367 (7) | |
C3 | 0.8922 (2) | 0.1066 (2) | 0.25163 (10) | 0.0402 (5) | |
C4 | 0.8914 (2) | 0.2119 (2) | 0.25372 (12) | 0.0519 (6) | |
H4 | 0.8206 | 0.2131 | 0.2575 | 0.062* | |
C5 | 1.0000 | 0.3163 (2) | 0.2500 | 0.0556 (10) | |
H5 | 1.0000 | 0.3878 | 0.2500 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0361 (5) | 0.0361 (5) | 0.0397 (7) | 0.0180 (2) | 0.000 | 0.000 |
F1 | 0.0564 (9) | 0.0450 (8) | 0.0602 (9) | 0.0226 (7) | −0.0068 (7) | −0.0151 (6) |
O1 | 0.0426 (9) | 0.0588 (14) | 0.0423 (12) | 0.0294 (7) | 0.0011 (5) | 0.0022 (10) |
C1 | 0.038 (2) | 0.038 (2) | 0.024 (2) | 0.0189 (8) | 0.000 | 0.000 |
C2 | 0.043 (2) | 0.0397 (12) | 0.0286 (13) | 0.0215 (9) | 0.0006 (13) | 0.0003 (6) |
C3 | 0.0495 (14) | 0.0460 (13) | 0.0309 (10) | 0.0283 (11) | −0.0004 (9) | 0.0012 (9) |
C4 | 0.072 (2) | 0.066 (2) | 0.0385 (12) | 0.0503 (15) | −0.0041 (12) | −0.0035 (12) |
C5 | 0.091 (3) | 0.0497 (13) | 0.040 (2) | 0.0453 (15) | −0.013 (2) | −0.0063 (9) |
Geometric parameters (Å, º) top
P1—F1 | 1.5977 (12) | C1—C2vii | 1.388 (3) |
P1—F1i | 1.5977 (12) | C1—C2viii | 1.388 (3) |
P1—F1ii | 1.5977 (12) | C1—C2 | 1.388 (3) |
P1—F1iii | 1.5977 (12) | C2—C3ix | 1.400 (2) |
P1—F1iv | 1.5977 (12) | C2—C3 | 1.400 (2) |
P1—F1v | 1.5977 (12) | C3—C4 | 1.374 (3) |
O1—C3 | 1.381 (2) | C4—C5 | 1.386 (3) |
O1—C3vi | 1.381 (2) | C5—C4ix | 1.386 (3) |
| | | |
F1—P1—F1i | 89.91 (7) | F1iv—P1—F1v | 180.0 |
F1—P1—F1ii | 180.0 | C3—O1—C3vi | 120.6 (2) |
F1i—P1—F1ii | 90.09 (7) | C2vii—C1—C2viii | 120.0 |
F1—P1—F1iii | 90.09 (7) | C2vii—C1—C2 | 120.0 |
F1i—P1—F1iii | 180.0 | C2viii—C1—C2 | 120.0 |
F1ii—P1—F1iii | 89.91 (7) | C1—C2—C3ix | 119.90 (15) |
F1—P1—F1iv | 89.91 (7) | C1—C2—C3 | 119.90 (15) |
F1i—P1—F1iv | 90.09 (7) | C3ix—C2—C3 | 120.2 (3) |
F1ii—P1—F1iv | 90.09 (7) | C4—C3—O1 | 120.0 (2) |
F1iii—P1—F1iv | 89.91 (7) | C4—C3—C2 | 120.3 (3) |
F1—P1—F1v | 90.09 (7) | O1—C3—C2 | 119.7 (2) |
F1i—P1—F1v | 89.91 (7) | C3—C4—C5 | 117.6 (2) |
F1ii—P1—F1v | 89.91 (7) | C4—C5—C4ix | 124.0 (3) |
F1iii—P1—F1v | 90.09 (7) | | |
Symmetry codes: (i) x−y, x, −z; (ii) −x, −y, −z; (iii) −x+y, −x, z; (iv) y, −x+y, −z; (v) −y, x−y, z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6220K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.733 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 13.015 (2) Å | T = 220 K |
c = 16.859 (3) Å | Prism, orange |
V = 2473.3 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 380 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8196 measured reflections | k = −16→16 |
567 independent reflections | l = −21→21 |
Refinement top
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
566 reflections | (Δ/σ)max = −0.010 |
47 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 1 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0413 (4) | |
F1 | 0.04933 (13) | 0.11536 (11) | 0.05450 (8) | 0.0619 (5) | |
O1 | 0.7865 (2) | 0.0000 | 0.2500 | 0.0518 (6) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0371 (10) | |
C2 | 1.0000 | 0.1068 (2) | 0.2500 | 0.0408 (7) | |
C3 | 0.8922 (2) | 0.1062 (2) | 0.25163 (11) | 0.0452 (5) | |
C4 | 0.8916 (2) | 0.2113 (2) | 0.25375 (12) | 0.0583 (7) | |
H4 | 0.8209 | 0.2125 | 0.2576 | 0.070* | |
C5 | 1.0000 | 0.3157 (3) | 0.2500 | 0.0639 (11) | |
H5 | 1.0000 | 0.3872 | 0.2500 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0400 (5) | 0.0400 (5) | 0.0440 (7) | 0.0200 (2) | 0.000 | 0.000 |
F1 | 0.0641 (9) | 0.0507 (8) | 0.0674 (9) | 0.0261 (7) | −0.0070 (7) | −0.0167 (6) |
O1 | 0.0466 (9) | 0.067 (2) | 0.0484 (12) | 0.0337 (8) | 0.0019 (6) | 0.0037 (11) |
C1 | 0.042 (2) | 0.042 (2) | 0.027 (2) | 0.0212 (8) | 0.000 | 0.000 |
C2 | 0.049 (2) | 0.0452 (12) | 0.0296 (13) | 0.0244 (9) | 0.0009 (13) | 0.0004 (7) |
C3 | 0.0550 (15) | 0.0521 (14) | 0.0347 (10) | 0.0315 (11) | −0.0003 (10) | 0.0010 (10) |
C4 | 0.083 (2) | 0.073 (2) | 0.0432 (12) | 0.057 (2) | −0.0062 (13) | −0.0048 (12) |
C5 | 0.104 (3) | 0.0553 (14) | 0.049 (2) | 0.052 (2) | −0.015 (2) | −0.0076 (10) |
Geometric parameters (Å, º) top
P1—F1 | 1.5959 (12) | C1—C2vii | 1.391 (3) |
P1—F1i | 1.5959 (12) | C1—C2 | 1.391 (3) |
P1—F1ii | 1.5959 (12) | C1—C2viii | 1.391 (3) |
P1—F1iii | 1.5959 (12) | C2—C3ix | 1.399 (2) |
P1—F1iv | 1.5959 (12) | C2—C3 | 1.399 (2) |
P1—F1v | 1.5959 (12) | C3—C4 | 1.373 (3) |
O1—C3 | 1.379 (3) | C4—C5 | 1.387 (3) |
O1—C3vi | 1.379 (3) | C5—C4ix | 1.387 (3) |
| | | |
F1—P1—F1i | 89.84 (7) | F1iv—P1—F1v | 180.0 |
F1—P1—F1ii | 90.16 (7) | C3—O1—C3vi | 120.5 (2) |
F1i—P1—F1ii | 180.0 | C2vii—C1—C2 | 120.0 |
F1—P1—F1iii | 180.0 | C2vii—C1—C2viii | 120.0 |
F1i—P1—F1iii | 90.16 (7) | C2—C1—C2viii | 120.0 |
F1ii—P1—F1iii | 89.84 (7) | C1—C2—C3ix | 119.7 (2) |
F1—P1—F1iv | 90.16 (7) | C1—C2—C3 | 119.7 (2) |
F1i—P1—F1iv | 89.84 (7) | C3ix—C2—C3 | 120.7 (3) |
F1ii—P1—F1iv | 90.16 (7) | C4—C3—O1 | 119.9 (2) |
F1iii—P1—F1iv | 89.84 (7) | C4—C3—C2 | 120.0 (3) |
F1—P1—F1v | 89.84 (7) | O1—C3—C2 | 120.1 (2) |
F1i—P1—F1v | 90.16 (7) | C3—C4—C5 | 117.7 (3) |
F1ii—P1—F1v | 89.84 (7) | C4—C5—C4ix | 123.8 (3) |
F1iii—P1—F1v | 90.16 (7) | | |
Symmetry codes: (i) x−y, x, −z; (ii) −x+y, −x, z; (iii) −x, −y, −z; (iv) −y, x−y, z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6243K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.724 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 13.040 (2) Å | T = 243 K |
c = 16.884 (3) Å | Prism, orange |
V = 2486.5 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 352 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8207 measured reflections | k = −16→15 |
569 independent reflections | l = −21→21 |
Refinement top
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
569 reflections | (Δ/σ)max = −0.023 |
47 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0470 (4) | |
F1 | 0.04927 (13) | 0.11510 (11) | 0.05442 (8) | 0.0707 (5) | |
O1 | 0.7870 (2) | 0.0000 | 0.2500 | 0.0589 (6) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0402 (10) | |
C2 | 1.0000 | 0.1067 (2) | 0.2500 | 0.0463 (7) | |
C3 | 0.8924 (2) | 0.1059 (2) | 0.25163 (11) | 0.0518 (6) | |
C4 | 0.8918 (2) | 0.2111 (2) | 0.25370 (12) | 0.0664 (7) | |
H4 | 0.8214 | 0.2126 | 0.2574 | 0.080* | |
C5 | 1.0000 | 0.3145 (3) | 0.2500 | 0.0711 (11) | |
H5 | 1.0000 | 0.3858 | 0.2500 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0463 (5) | 0.0463 (5) | 0.0484 (7) | 0.0231 (2) | 0.000 | 0.000 |
F1 | 0.0743 (10) | 0.0576 (8) | 0.0751 (10) | 0.0292 (8) | −0.0084 (7) | −0.0195 (6) |
O1 | 0.0533 (9) | 0.076 (2) | 0.0554 (13) | 0.0378 (8) | 0.0018 (6) | 0.0036 (12) |
C1 | 0.046 (2) | 0.046 (2) | 0.029 (2) | 0.0229 (8) | 0.000 | 0.000 |
C2 | 0.056 (2) | 0.0509 (13) | 0.0334 (13) | 0.0281 (9) | 0.0022 (14) | 0.0011 (7) |
C3 | 0.061 (2) | 0.0635 (15) | 0.0388 (10) | 0.0375 (12) | −0.0001 (11) | 0.0008 (10) |
C4 | 0.092 (2) | 0.085 (2) | 0.0501 (13) | 0.065 (2) | −0.0075 (13) | −0.0068 (13) |
C5 | 0.118 (4) | 0.0630 (15) | 0.051 (2) | 0.059 (2) | −0.018 (2) | −0.0091 (10) |
Geometric parameters (Å, º) top
P1—F1 | 1.5954 (12) | C1—C2vii | 1.391 (3) |
P1—F1i | 1.5954 (12) | C1—C2 | 1.391 (3) |
P1—F1ii | 1.5954 (12) | C1—C2viii | 1.391 (3) |
P1—F1iii | 1.5954 (12) | C2—C3ix | 1.398 (2) |
P1—F1iv | 1.5954 (12) | C2—C3 | 1.398 (2) |
P1—F1v | 1.5954 (12) | C3—C4 | 1.377 (3) |
O1—C3vi | 1.377 (3) | C4—C5 | 1.382 (3) |
O1—C3 | 1.377 (3) | C5—C4ix | 1.382 (3) |
| | | |
F1—P1—F1i | 180.0 | F1iv—P1—F1v | 90.14 (7) |
F1—P1—F1ii | 90.14 (7) | C3vi—O1—C3 | 120.5 (2) |
F1i—P1—F1ii | 89.86 (7) | C2vii—C1—C2 | 120.0 |
F1—P1—F1iii | 90.14 (7) | C2vii—C1—C2viii | 120.0 |
F1i—P1—F1iii | 89.86 (7) | C2—C1—C2viii | 120.0 |
F1ii—P1—F1iii | 90.14 (7) | C1—C2—C3ix | 119.6 (2) |
F1—P1—F1iv | 89.86 (7) | C1—C2—C3 | 119.6 (2) |
F1i—P1—F1iv | 90.14 (7) | C3ix—C2—C3 | 120.8 (3) |
F1ii—P1—F1iv | 180.0 | C4—C3—O1 | 120.0 (2) |
F1iii—P1—F1iv | 89.86 (7) | C4—C3—C2 | 119.9 (3) |
F1—P1—F1v | 89.86 (7) | O1—C3—C2 | 120.1 (2) |
F1i—P1—F1v | 90.14 (7) | C3—C4—C5 | 117.3 (3) |
F1ii—P1—F1v | 89.86 (7) | C4—C5—C4ix | 124.6 (3) |
F1iii—P1—F1v | 180.0 | | |
Symmetry codes: (i) −x, −y, −z; (ii) −x+y, −x, z; (iii) −y, x−y, z; (iv) x−y, x, −z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6268K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.714 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 13.067 (2) Å | T = 268 K |
c = 16.910 (3) Å | Prism, orange |
V = 2500.4 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 352 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8252 measured reflections | k = −16→16 |
572 independent reflections | l = −21→21 |
Refinement top
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) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
571 reflections | (Δ/σ)max = −0.040 |
47 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 1 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0530 (5) | |
F1 | 0.0491 (2) | 0.11466 (13) | 0.05418 (9) | 0.0801 (6) | |
O1 | 0.7875 (2) | 0.0000 | 0.2500 | 0.0667 (8) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0453 (13) | |
C2 | 1.0000 | 0.1064 (3) | 0.2500 | 0.0516 (8) | |
C3 | 0.8925 (3) | 0.1056 (3) | 0.25161 (13) | 0.0579 (7) | |
C4 | 0.8923 (3) | 0.2108 (3) | 0.25373 (15) | 0.0753 (9) | |
H4 | 0.8221 | 0.2122 | 0.2575 | 0.090* | |
C5 | 1.0000 | 0.3140 (3) | 0.2500 | 0.0819 (14) | |
H5 | 1.0000 | 0.3852 | 0.2500 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0520 (6) | 0.0520 (6) | 0.0549 (9) | 0.0260 (3) | 0.000 | 0.000 |
F1 | 0.0858 (13) | 0.0642 (10) | 0.0849 (12) | 0.0334 (10) | −0.0104 (9) | −0.0231 (8) |
O1 | 0.0609 (12) | 0.087 (2) | 0.061 (2) | 0.0435 (10) | 0.0021 (7) | 0.0041 (15) |
C1 | 0.052 (2) | 0.052 (2) | 0.033 (3) | 0.0258 (10) | 0.000 | 0.000 |
C2 | 0.060 (2) | 0.056 (2) | 0.040 (2) | 0.0301 (11) | 0.003 (2) | 0.0016 (9) |
C3 | 0.069 (2) | 0.070 (2) | 0.0436 (13) | 0.041 (2) | −0.0010 (13) | −0.0001 (13) |
C4 | 0.107 (3) | 0.097 (2) | 0.055 (2) | 0.075 (2) | −0.008 (2) | −0.006 (2) |
C5 | 0.133 (5) | 0.073 (2) | 0.060 (2) | 0.067 (2) | −0.019 (3) | −0.0093 (14) |
Geometric parameters (Å, º) top
P1—F1i | 1.5920 (14) | C1—C2vii | 1.390 (4) |
P1—F1 | 1.5920 (14) | C1—C2viii | 1.390 (4) |
P1—F1ii | 1.5920 (14) | C1—C2 | 1.390 (4) |
P1—F1iii | 1.5920 (14) | C2—C3ix | 1.400 (3) |
P1—F1iv | 1.5920 (14) | C2—C3 | 1.400 (3) |
P1—F1v | 1.5920 (14) | C3—C4 | 1.376 (4) |
O1—C3 | 1.377 (3) | C4—C5 | 1.380 (4) |
O1—C3vi | 1.377 (3) | C5—C4ix | 1.380 (4) |
| | | |
F1i—P1—F1 | 180.0 | F1iv—P1—F1v | 90.18 (8) |
F1i—P1—F1ii | 89.82 (8) | C3—O1—C3vi | 120.6 (3) |
F1—P1—F1ii | 90.18 (8) | C2vii—C1—C2viii | 120.0 |
F1i—P1—F1iii | 89.82 (8) | C2vii—C1—C2 | 120.0 |
F1—P1—F1iii | 90.18 (8) | C2viii—C1—C2 | 120.0 |
F1ii—P1—F1iii | 90.18 (8) | C1—C2—C3ix | 119.6 (2) |
F1i—P1—F1iv | 90.18 (8) | C1—C2—C3 | 119.6 (2) |
F1—P1—F1iv | 89.82 (8) | C3ix—C2—C3 | 120.7 (4) |
F1ii—P1—F1iv | 180.0 | C4—C3—O1 | 120.2 (3) |
F1iii—P1—F1iv | 89.82 (8) | C4—C3—C2 | 119.8 (3) |
F1i—P1—F1v | 90.18 (8) | O1—C3—C2 | 120.0 (3) |
F1—P1—F1v | 89.82 (8) | C3—C4—C5 | 117.7 (3) |
F1ii—P1—F1v | 89.82 (8) | C4—C5—C4ix | 124.2 (4) |
F1iii—P1—F1v | 180.0 | | |
Symmetry codes: (i) −x, −y, −z; (ii) −x+y, −x, z; (iii) −y, x−y, z; (iv) x−y, x, −z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6293K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.705 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 13.094 (2) Å | T = 293 K |
c = 16.937 (3) Å | Prism, orange |
V = 2514.7 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 310 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.067 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8328 measured reflections | k = −16→16 |
575 independent reflections | l = −21→21 |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P] where P = (Fo2 + 2Fc2)/3 |
575 reflections | (Δ/σ)max = −0.022 |
47 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0599 (5) | |
F1 | 0.0488 (2) | 0.11413 (13) | 0.05407 (9) | 0.0905 (7) | |
O1 | 0.7880 (2) | 0.0000 | 0.2500 | 0.0746 (8) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0516 (14) | |
C2 | 1.0000 | 0.1061 (3) | 0.2500 | 0.0584 (9) | |
C3 | 0.8929 (3) | 0.1055 (3) | 0.25153 (13) | 0.0652 (7) | |
C4 | 0.8928 (3) | 0.2105 (3) | 0.2535 (2) | 0.0848 (10) | |
H4 | 0.8227 | 0.2119 | 0.2572 | 0.102* | |
C5 | 1.0000 | 0.3134 (3) | 0.2500 | 0.095 (2) | |
H5 | 1.0000 | 0.3844 | 0.2500 | 0.114* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0593 (7) | 0.0593 (7) | 0.0611 (10) | 0.0297 (3) | 0.000 | 0.000 |
F1 | 0.0974 (14) | 0.0744 (11) | 0.0948 (13) | 0.0393 (11) | −0.0108 (10) | −0.0257 (8) |
O1 | 0.0682 (12) | 0.099 (2) | 0.067 (2) | 0.0493 (11) | 0.0020 (8) | 0.004 (2) |
C1 | 0.058 (2) | 0.058 (2) | 0.039 (3) | 0.0289 (11) | 0.000 | 0.000 |
C2 | 0.070 (3) | 0.064 (2) | 0.044 (2) | 0.0348 (13) | 0.001 (2) | 0.0003 (9) |
C3 | 0.079 (2) | 0.078 (2) | 0.0484 (14) | 0.047 (2) | −0.002 (2) | −0.0001 (15) |
C4 | 0.119 (3) | 0.110 (3) | 0.062 (2) | 0.085 (2) | −0.011 (2) | −0.010 (2) |
C5 | 0.157 (5) | 0.084 (2) | 0.067 (3) | 0.079 (3) | −0.024 (3) | −0.012 (2) |
Geometric parameters (Å, º) top
P1—F1i | 1.5891 (14) | C1—C2vii | 1.390 (4) |
P1—F1ii | 1.5891 (14) | C1—C2viii | 1.390 (4) |
P1—F1 | 1.5891 (14) | C1—C2 | 1.390 (4) |
P1—F1iii | 1.5891 (14) | C2—C3ix | 1.398 (3) |
P1—F1iv | 1.5891 (14) | C2—C3 | 1.398 (3) |
P1—F1v | 1.5891 (14) | C3—C4 | 1.375 (4) |
O1—C3 | 1.378 (3) | C4—C5 | 1.378 (4) |
O1—C3vi | 1.378 (3) | C5—C4ix | 1.378 (4) |
| | | |
F1i—P1—F1ii | 90.11 (8) | F1iv—P1—F1v | 180.0 |
F1i—P1—F1 | 180.0 | C3—O1—C3vi | 120.6 (3) |
F1ii—P1—F1 | 89.89 (8) | C2vii—C1—C2viii | 120.0 |
F1i—P1—F1iii | 89.89 (8) | C2vii—C1—C2 | 120.0 |
F1ii—P1—F1iii | 180.0 | C2viii—C1—C2 | 120.0 |
F1—P1—F1iii | 90.11 (8) | C1—C2—C3ix | 119.7 (2) |
F1i—P1—F1iv | 90.11 (8) | C1—C2—C3 | 119.7 (2) |
F1ii—P1—F1iv | 90.11 (8) | C3ix—C2—C3 | 120.6 (4) |
F1—P1—F1iv | 89.89 (8) | C4—C3—O1 | 120.3 (3) |
F1iii—P1—F1iv | 89.89 (8) | C4—C3—C2 | 119.8 (4) |
F1i—P1—F1v | 89.89 (8) | O1—C3—C2 | 120.0 (3) |
F1ii—P1—F1v | 89.89 (8) | C3—C4—C5 | 117.9 (4) |
F1—P1—F1v | 90.11 (8) | C4—C5—C4ix | 124.0 (4) |
F1iii—P1—F1v | 90.11 (8) | | |
Symmetry codes: (i) −x, −y, −z; (ii) x−y, x, −z; (iii) −x+y, −x, z; (iv) y, −x+y, −z; (v) −y, x−y, z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6313K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.699 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 13.111 (2) Å | T = 313 K |
c = 16.953 (3) Å | Prism, orange |
V = 2523.6 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 303 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.067 |
Graphite monochromator | θmax = 26.3°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8369 measured reflections | k = −16→16 |
577 independent reflections | l = −21→21 |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 1.2721P] where P = (Fo2 + 2Fc2)/3 |
576 reflections | (Δ/σ)max = 0.003 |
47 parameters | Δρmax = 0.10 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 1 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0643 (5) | |
F1 | 0.0486 (2) | 0.11406 (13) | 0.05391 (9) | 0.0998 (7) | |
O1 | 0.7886 (2) | 0.0000 | 0.2500 | 0.0808 (8) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0555 (13) | |
C2 | 1.0000 | 0.1063 (3) | 0.2500 | 0.0626 (9) | |
C3 | 0.8930 (3) | 0.1053 (3) | 0.25162 (12) | 0.0711 (7) | |
C4 | 0.8923 (3) | 0.2093 (3) | 0.25351 (15) | 0.0934 (10) | |
H4 | 0.8222 | 0.2106 | 0.2570 | 0.112* | |
C5 | 1.0000 | 0.3127 (3) | 0.2500 | 0.104 (2) | |
H5 | 1.0000 | 0.3836 | 0.2500 | 0.125* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0634 (7) | 0.0634 (7) | 0.0662 (9) | 0.0317 (3) | 0.000 | 0.000 |
F1 | 0.1059 (14) | 0.0818 (11) | 0.1048 (13) | 0.0418 (11) | −0.0121 (10) | −0.0294 (8) |
O1 | 0.0744 (12) | 0.106 (2) | 0.073 (2) | 0.0529 (11) | 0.0009 (8) | 0.002 (2) |
C1 | 0.064 (2) | 0.064 (2) | 0.038 (3) | 0.0321 (11) | 0.000 | 0.000 |
C2 | 0.077 (3) | 0.068 (2) | 0.046 (2) | 0.0386 (13) | 0.001 (2) | 0.0006 (9) |
C3 | 0.089 (2) | 0.088 (2) | 0.0513 (13) | 0.055 (2) | −0.004 (2) | −0.0010 (14) |
C4 | 0.133 (3) | 0.120 (3) | 0.067 (2) | 0.093 (2) | −0.009 (2) | −0.009 (2) |
C5 | 0.172 (5) | 0.093 (2) | 0.073 (3) | 0.086 (3) | −0.027 (3) | −0.013 (2) |
Geometric parameters (Å, º) top
P1—F1i | 1.5889 (14) | C1—C2vii | 1.394 (4) |
P1—F1 | 1.5889 (14) | C1—C2 | 1.394 (4) |
P1—F1ii | 1.5889 (14) | C1—C2viii | 1.394 (4) |
P1—F1iii | 1.5889 (14) | C2—C3ix | 1.397 (3) |
P1—F1iv | 1.5889 (14) | C2—C3 | 1.397 (3) |
P1—F1v | 1.5889 (14) | C3—C4 | 1.369 (4) |
O1—C3 | 1.375 (3) | C4—C5 | 1.385 (4) |
O1—C3vi | 1.375 (3) | C5—C4ix | 1.385 (4) |
| | | |
F1i—P1—F1 | 180.0 | F1iv—P1—F1v | 180.0 |
F1i—P1—F1ii | 90.21 (8) | C3—O1—C3vi | 120.9 (3) |
F1—P1—F1ii | 89.79 (8) | C2vii—C1—C2 | 120.0 |
F1i—P1—F1iii | 89.79 (8) | C2vii—C1—C2viii | 120.0 |
F1—P1—F1iii | 90.21 (8) | C2—C1—C2viii | 120.000 (1) |
F1ii—P1—F1iii | 180.0 | C1—C2—C3ix | 119.5 (2) |
F1i—P1—F1iv | 89.79 (8) | C1—C2—C3 | 119.5 (2) |
F1—P1—F1iv | 90.21 (8) | C3ix—C2—C3 | 120.9 (4) |
F1ii—P1—F1iv | 89.79 (8) | C4—C3—O1 | 120.1 (3) |
F1iii—P1—F1iv | 90.21 (8) | C4—C3—C2 | 119.9 (4) |
F1i—P1—F1v | 90.21 (8) | O1—C3—C2 | 120.0 (3) |
F1—P1—F1v | 89.79 (8) | C3—C4—C5 | 117.6 (4) |
F1ii—P1—F1v | 90.21 (8) | C4—C5—C4ix | 124.1 (4) |
F1iii—P1—F1v | 89.79 (8) | | |
Symmetry codes: (i) −x, −y, −z; (ii) x−y, x, −z; (iii) −x+y, −x, z; (iv) −y, x−y, z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6338K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.692 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.25 mm−1 |
a = 13.131 (2) Å | T = 338 K |
c = 16.970 (3) Å | Prism, orange |
V = 2534.0 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 275 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.071 |
Graphite monochromator | θmax = 26.4°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8356 measured reflections | k = −16→15 |
579 independent reflections | l = −21→21 |
Refinement top
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) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 1.2721P] where P = (Fo2 + 2Fc2)/3 |
579 reflections | (Δ/σ)max = −0.028 |
47 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0720 (6) | |
F1 | 0.0483 (2) | 0.11356 (14) | 0.05367 (9) | 0.1126 (8) | |
O1 | 0.7892 (2) | 0.0000 | 0.2500 | 0.0917 (9) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.0620 (15) | |
C2 | 1.0000 | 0.1056 (3) | 0.2500 | 0.0688 (10) | |
C3 | 0.8935 (3) | 0.1050 (3) | 0.25159 (13) | 0.0800 (8) | |
C4 | 0.8925 (3) | 0.2090 (4) | 0.2537 (2) | 0.1036 (12) | |
H4 | 0.8226 | 0.2104 | 0.2574 | 0.124* | |
C5 | 1.0000 | 0.3114 (4) | 0.2500 | 0.117 (2) | |
H5 | 1.0000 | 0.3822 | 0.2500 | 0.140* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0726 (8) | 0.0726 (8) | 0.0708 (10) | 0.0363 (4) | 0.000 | 0.000 |
F1 | 0.121 (2) | 0.0923 (12) | 0.1163 (15) | 0.0475 (13) | −0.0134 (11) | −0.0324 (9) |
O1 | 0.0845 (14) | 0.122 (3) | 0.081 (2) | 0.0611 (14) | 0.0011 (10) | 0.002 (2) |
C1 | 0.071 (2) | 0.071 (2) | 0.045 (3) | 0.0353 (12) | 0.000 | 0.000 |
C2 | 0.082 (3) | 0.075 (2) | 0.051 (2) | 0.0411 (14) | 0.002 (2) | 0.0010 (10) |
C3 | 0.101 (3) | 0.098 (3) | 0.0561 (15) | 0.060 (2) | 0.000 (2) | −0.001 (2) |
C4 | 0.147 (4) | 0.132 (3) | 0.075 (2) | 0.102 (3) | −0.011 (2) | −0.012 (2) |
C5 | 0.196 (7) | 0.105 (2) | 0.079 (3) | 0.098 (3) | −0.030 (4) | −0.015 (2) |
Geometric parameters (Å, º) top
P1—F1i | 1.584 (2) | C1—C2vii | 1.387 (4) |
P1—F1 | 1.584 (2) | C1—C2 | 1.387 (4) |
P1—F1ii | 1.584 (2) | C1—C2viii | 1.387 (4) |
P1—F1iii | 1.584 (2) | C2—C3ix | 1.394 (3) |
P1—F1iv | 1.584 (2) | C2—C3 | 1.394 (3) |
P1—F1v | 1.584 (2) | C3—C4 | 1.373 (4) |
O1—C3vi | 1.374 (4) | C4—C5 | 1.381 (4) |
O1—C3 | 1.374 (4) | C5—C4ix | 1.381 (4) |
| | | |
F1i—P1—F1 | 180.0 | F1iv—P1—F1v | 89.76 (9) |
F1i—P1—F1ii | 90.24 (9) | C3vi—O1—C3 | 120.6 (3) |
F1—P1—F1ii | 89.76 (9) | C2vii—C1—C2 | 120.0 |
F1i—P1—F1iii | 89.76 (9) | C2vii—C1—C2viii | 120.0 |
F1—P1—F1iii | 90.24 (9) | C2—C1—C2viii | 120.000 (1) |
F1ii—P1—F1iii | 89.76 (9) | C1—C2—C3ix | 119.7 (2) |
F1i—P1—F1iv | 89.76 (9) | C1—C2—C3 | 119.7 (2) |
F1—P1—F1iv | 90.24 (9) | C3ix—C2—C3 | 120.6 (5) |
F1ii—P1—F1iv | 180.0 | C4—C3—O1 | 119.8 (3) |
F1iii—P1—F1iv | 90.24 (9) | C4—C3—C2 | 120.2 (4) |
F1i—P1—F1v | 90.24 (9) | O1—C3—C2 | 120.0 (3) |
F1—P1—F1v | 89.76 (9) | C3—C4—C5 | 117.0 (4) |
F1ii—P1—F1v | 90.24 (9) | C4—C5—C4ix | 124.8 (5) |
F1iii—P1—F1v | 180.0 | | |
Symmetry codes: (i) −x, −y, −z; (ii) x−y, x, −z; (iii) −y, x−y, z; (iv) −x+y, −x, z; (v) y, −x+y, −z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |
(6373K) 4,8,12-trioxa-4,8,12,12
c-tetrahydro-dibenzo[cd,mn]pyrenium
hexafluorophosphate
top
Crystal data top
C19H9O3·F6P | F(000) = 1296 |
Mr = 430.23 | Dx = 1.673 Mg m−3 |
Trigonal, R3c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -R 3 2"c | µ = 0.24 mm−1 |
a = 13.181 (2) Å | T = 373 K |
c = 17.025 (3) Å | Prism, orange |
V = 2561.6 (7) Å3 | 0.25 × 0.25 × 0.08 mm |
Z = 6 | |
Data collection top
Siemens SMART CCD diffractometer | 249 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.080 |
Graphite monochromator | θmax = 26.3°, θmin = 3.0° |
ω scan, frame data integration | h = −16→16 |
8443 measured reflections | k = −16→15 |
586 independent reflections | l = −21→21 |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 1.2721P] where P = (Fo2 + 2Fc2)/3 |
586 reflections | (Δ/σ)max = 0.078 |
47 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.10 e Å−3 |
Special details top
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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.0000 | 0.0000 | 0.0000 | 0.0833 (7) | |
F1 | 0.0478 (2) | 0.1127 (2) | 0.05332 (11) | 0.1329 (10) | |
O1 | 0.7903 (2) | 0.0000 | 0.2500 | 0.1058 (11) | |
C1 | 1.0000 | 0.0000 | 0.2500 | 0.073 (2) | |
C2 | 1.0000 | 0.1046 (4) | 0.2500 | 0.0798 (12) | |
C3 | 0.8941 (4) | 0.1048 (4) | 0.25148 (15) | 0.0943 (10) | |
C4 | 0.8933 (4) | 0.2087 (4) | 0.2532 (2) | 0.124 (2) | |
H4 | 0.8236 | 0.2101 | 0.2564 | 0.149* | |
C5 | 1.0000 | 0.3105 (5) | 0.2500 | 0.141 (3) | |
H5 | 1.0000 | 0.3811 | 0.2500 | 0.169* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0845 (9) | 0.0845 (9) | 0.0810 (12) | 0.0422 (5) | 0.000 | 0.000 |
F1 | 0.143 (2) | 0.1106 (14) | 0.135 (2) | 0.056 (2) | −0.0130 (14) | −0.0392 (11) |
O1 | 0.098 (2) | 0.142 (3) | 0.092 (2) | 0.071 (2) | 0.0005 (12) | 0.001 (2) |
C1 | 0.083 (3) | 0.083 (3) | 0.053 (4) | 0.0417 (14) | 0.000 | 0.000 |
C2 | 0.090 (3) | 0.087 (2) | 0.063 (2) | 0.045 (2) | 0.000 (2) | 0.0001 (12) |
C3 | 0.121 (4) | 0.113 (3) | 0.065 (2) | 0.070 (3) | −0.003 (2) | 0.000 (2) |
C4 | 0.184 (5) | 0.157 (4) | 0.088 (2) | 0.128 (4) | −0.020 (3) | −0.017 (3) |
C5 | 0.247 (10) | 0.128 (3) | 0.088 (4) | 0.124 (5) | −0.039 (6) | −0.019 (3) |
Geometric parameters (Å, º) top
P1—F1i | 1.579 (2) | C1—C2vii | 1.379 (5) |
P1—F1 | 1.579 (2) | C1—C2viii | 1.379 (5) |
P1—F1ii | 1.579 (2) | C1—C2 | 1.379 (5) |
P1—F1iii | 1.579 (2) | C2—C3ix | 1.398 (4) |
P1—F1iv | 1.579 (2) | C2—C3 | 1.398 (4) |
P1—F1v | 1.579 (2) | C3—C4 | 1.375 (5) |
O1—C3vi | 1.375 (4) | C4—C5 | 1.376 (5) |
O1—C3 | 1.375 (4) | C5—C4ix | 1.376 (5) |
| | | |
F1i—P1—F1 | 180.0 | F1iv—P1—F1v | 90.24 (10) |
F1i—P1—F1ii | 90.24 (10) | C3vi—O1—C3 | 121.0 (4) |
F1—P1—F1ii | 89.76 (10) | C2vii—C1—C2viii | 120.0 |
F1i—P1—F1iii | 90.24 (10) | C2vii—C1—C2 | 120.0 |
F1—P1—F1iii | 89.76 (10) | C2viii—C1—C2 | 120.000 (1) |
F1ii—P1—F1iii | 90.24 (10) | C1—C2—C3ix | 120.1 (3) |
F1i—P1—F1iv | 89.76 (10) | C1—C2—C3 | 120.1 (3) |
F1—P1—F1iv | 90.24 (10) | C3ix—C2—C3 | 119.8 (6) |
F1ii—P1—F1iv | 89.76 (10) | C4—C3—O1 | 120.1 (4) |
F1iii—P1—F1iv | 180.0 | C4—C3—C2 | 120.5 (5) |
F1i—P1—F1v | 89.76 (10) | O1—C3—C2 | 119.4 (4) |
F1—P1—F1v | 90.24 (10) | C3—C4—C5 | 117.2 (6) |
F1ii—P1—F1v | 180.0 | C4—C5—C4ix | 124.7 (7) |
F1iii—P1—F1v | 89.76 (10) | | |
Symmetry codes: (i) −x, −y, −z; (ii) x−y, x, −z; (iii) y, −x+y, −z; (iv) −y, x−y, z; (v) −x+y, −x, z; (vi) x−y, −y, −z+1/2; (vii) −y+1, x−y−1, z; (viii) −x+y+2, −x+1, z; (ix) −x+2, −x+y+1, −z+1/2. |