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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[cdmn]pyrenylium cations with the monovalent anions I-, BF_4^-, PF_6^-, AsF_6^-, HNO3.NO_3^- and CF3SO_3^-, and the divalent anions S2O_6^{2-} and Mo6Cl_{14}^{2-}. 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 R3c 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 (P21/n, P21/c and C2/c), but also P1.

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Contains datablocks 3, 4, 5, 6120K, 7, 8, 9, 10, 11, 12, 6160K, 6198K, 6220K, 6243K, 6268K, 6293K, 6313K, 6338K, 6373K, global

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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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Structure factor file (SHELXL table format)
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CCDC references: 131774; 131775; 131776; 131777; 131778; 131779; 131780; 131781; 131782; 131783; 131784; 131785; 131786; 131787; 131788; 131789; 131790; 131791; 131792

Computing details top

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-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium iodide top
Crystal data top
C19H9O3·IZ = 8
Mr = 412.16F(000) = 1600
Orthorhombic, PbcaDx = 1.810 Mg m3
Hall symbol: -P 2ac 2abMo Kα radiation, λ = 0.71073 Å
a = 12.934 (3) ŵ = 2.13 mm1
b = 14.748 (3) ÅT = 293 K
c = 15.858 (3) ÅCube, dark red
V = 3024.9 (10) Å30.32 × 0.30 × 0.30 mm
Data collection top
Siemens SMART CCD
diffractometer
3093 independent reflections
Radiation source: fine-focus sealed tube2679 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scan, frame data integrationθmax = 26.4°, θmin = 2.5°
Absorption correction: empirical (using intensity measurements)h = 1616
Tmin = 0.476, Tmax = 0.603k = 1818
29370 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.20Calculated w = 1/[σ2(Fo2) + (0.0552P)2 + 2.1435P]
where P = (Fo2 + 2Fc2)/3
3093 reflections(Δ/σ)max = 0.003
209 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 1.74 e Å3
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
xyzUiso*/Ueq
C10.8724 (2)0.6351 (2)0.7442 (2)0.0441 (7)
C20.9012 (3)0.5494 (2)0.7160 (2)0.0465 (7)
C30.9530 (3)0.5411 (3)0.6391 (2)0.0519 (8)
C40.9804 (4)0.4568 (3)0.6105 (2)0.0644 (10)
H41.01660.44980.56020.077*
C50.9525 (4)0.3824 (3)0.6584 (3)0.0641 (10)
H50.96970.32510.63830.077*
C60.9011 (3)0.3884 (3)0.7338 (3)0.0587 (9)
H60.88340.33640.76380.070*
C70.8763 (2)0.4731 (3)0.7639 (2)0.0512 (8)
C80.8207 (3)0.6440 (2)0.8205 (2)0.0476 (7)
C90.8002 (3)0.5673 (3)0.8695 (2)0.0541 (9)
C100.7532 (4)0.5760 (3)0.9466 (2)0.0687 (10)
H100.73960.52570.98020.082*
C110.7267 (3)0.6628 (4)0.9724 (3)0.0753 (12)
H110.69490.66921.02470.090*
C120.7441 (3)0.7402 (3)0.9260 (2)0.0650 (10)
H120.72420.79690.94590.078*
C130.7921 (3)0.7307 (3)0.8488 (2)0.0536 (8)
C140.8935 (2)0.7111 (2)0.6959 (2)0.0469 (7)
C150.8611 (3)0.7967 (3)0.7234 (2)0.0511 (8)
C160.8791 (3)0.8723 (2)0.6752 (3)0.0617 (10)
H160.85660.92930.69210.074*
C170.9324 (4)0.8600 (3)0.5997 (3)0.0645 (10)
H170.94630.91090.56710.077*
C180.9660 (3)0.7764 (3)0.5701 (2)0.0626 (10)
H181.00110.77130.51910.075*
C190.9454 (3)0.7018 (3)0.6186 (2)0.0531 (8)
O10.9754 (2)0.6168 (2)0.5923 (2)0.0605 (7)
O20.8272 (2)0.4824 (2)0.8404 (2)0.0581 (6)
O30.8128 (2)0.8055 (2)0.8003 (2)0.0579 (6)
I10.87640 (2)0.12899 (2)0.62911 (2)0.06149 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (2)0.049 (2)0.046 (2)0.0013 (13)0.0049 (13)0.0001 (13)
C20.047 (2)0.046 (2)0.046 (2)0.0021 (14)0.0040 (13)0.0022 (13)
C30.057 (2)0.052 (2)0.047 (2)0.004 (2)0.0028 (15)0.0004 (14)
C40.082 (3)0.061 (2)0.050 (2)0.012 (2)0.003 (2)0.010 (2)
C50.070 (3)0.051 (2)0.071 (2)0.011 (2)0.017 (2)0.011 (2)
C60.056 (2)0.047 (2)0.073 (2)0.005 (2)0.012 (2)0.004 (2)
C70.047 (2)0.052 (2)0.055 (2)0.0044 (14)0.0076 (15)0.002 (2)
C80.040 (2)0.056 (2)0.047 (2)0.0007 (14)0.0015 (13)0.0031 (14)
C90.045 (2)0.066 (2)0.051 (2)0.005 (2)0.0004 (14)0.004 (2)
C100.063 (2)0.085 (3)0.058 (2)0.003 (2)0.008 (2)0.011 (2)
C110.065 (3)0.106 (4)0.055 (2)0.007 (3)0.011 (2)0.009 (2)
C120.056 (2)0.079 (3)0.060 (2)0.008 (2)0.007 (2)0.014 (2)
C130.043 (2)0.061 (2)0.056 (2)0.003 (2)0.0013 (15)0.006 (2)
C140.043 (2)0.049 (2)0.049 (2)0.0015 (14)0.0016 (13)0.0013 (14)
C150.046 (2)0.050 (2)0.057 (2)0.0021 (14)0.0043 (15)0.000 (2)
C160.058 (2)0.048 (2)0.079 (3)0.002 (2)0.011 (2)0.003 (2)
C170.064 (3)0.058 (2)0.072 (2)0.006 (2)0.009 (2)0.017 (2)
C180.065 (2)0.066 (2)0.057 (2)0.003 (2)0.003 (2)0.014 (2)
C190.054 (2)0.054 (2)0.051 (2)0.002 (2)0.0016 (15)0.0005 (15)
O10.075 (2)0.0581 (15)0.0478 (13)0.0058 (13)0.0114 (12)0.0017 (11)
O20.061 (2)0.0552 (14)0.0579 (14)0.0067 (12)0.0051 (12)0.0083 (11)
O30.0576 (15)0.0519 (14)0.0641 (15)0.0071 (12)0.0032 (12)0.0067 (11)
I10.0620 (2)0.0500 (2)0.0724 (2)0.00363 (10)0.00786 (11)0.01283 (10)
Geometric parameters (Å, º) top
C1—C141.385 (5)C9—O21.379 (5)
C1—C81.388 (5)C10—C111.387 (7)
C1—C21.392 (5)C11—C121.377 (6)
C2—C71.396 (5)C12—C131.379 (5)
C2—C31.397 (5)C13—O31.372 (5)
C3—C41.371 (5)C14—C151.400 (5)
C3—O11.372 (4)C14—C191.403 (5)
C4—C51.382 (6)C15—C161.371 (5)
C5—C61.372 (7)C15—O31.376 (4)
C6—C71.376 (5)C16—C171.393 (7)
C7—O21.376 (4)C17—C181.389 (6)
C8—C91.398 (5)C18—C191.368 (5)
C8—C131.405 (5)C19—O11.377 (4)
C9—C101.371 (5)
C14—C1—C8120.1 (3)C9—C10—C11117.3 (4)
C14—C1—C2120.3 (3)C12—C11—C10124.5 (4)
C8—C1—C2119.6 (3)C11—C12—C13117.6 (4)
C1—C2—C7119.7 (3)O3—C13—C12120.2 (3)
C1—C2—C3119.2 (3)O3—C13—C8120.1 (3)
C7—C2—C3121.1 (3)C12—C13—C8119.7 (4)
C4—C3—O1120.3 (3)C1—C14—C15119.8 (3)
C4—C3—C2119.5 (4)C1—C14—C19119.9 (3)
O1—C3—C2120.2 (3)C15—C14—C19120.3 (3)
C3—C4—C5118.1 (4)C16—C15—O3119.7 (4)
C6—C5—C4123.7 (4)C16—C15—C14120.5 (4)
C5—C6—C7118.3 (4)O3—C15—C14119.8 (3)
O2—C7—C6120.3 (3)C15—C16—C17117.2 (4)
O2—C7—C2120.4 (3)C18—C17—C16124.1 (4)
C6—C7—C2119.3 (3)C19—C18—C17117.5 (4)
C1—C8—C9120.0 (3)C18—C19—O1120.4 (3)
C1—C8—C13119.4 (3)C18—C19—C14120.4 (4)
C9—C8—C13120.6 (3)O1—C19—C14119.3 (3)
C10—C9—O2119.7 (4)C3—O1—C19121.1 (3)
C10—C9—C8120.3 (4)C7—O2—C9120.1 (3)
O2—C9—C8120.0 (3)C13—O3—C15120.7 (3)
(4) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium tetrafluoroborate top
Crystal data top
C19H9O3·BF4Z = 8
Mr = 372.07F(000) = 1504
Orthorhombic, PbcaDx = 1.648 Mg m3
Hall symbol: -P 2ac 2abMo Kα radiation, λ = 0.71073 Å
a = 12.817 (3) ŵ = 0.14 mm1
b = 15.196 (3) ÅT = 120 K
c = 15.396 (3) ÅNeedle, orange
V = 2998.6 (10) Å30.45 × 0.25 × 0.10 mm
Data collection top
Siemens SMART CCD
diffractometer
3056 independent reflections
Radiation source: fine-focus sealed tube2381 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scan, frame data integrationθmax = 26.4°, θmin = 2.5°
Absorption correction: empirical (using intensity measurements)h = 1616
Tmin = 0.871, Tmax = 0.980k = 1818
29798 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.03Calculated w = 1/[σ2(Fo2) + (0.0561P)2 + 2.684P]
where P = (Fo2 + 2Fc2)/3
3054 reflections(Δ/σ)max = 0.004
244 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.52 e Å3
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
xyzUiso*/Ueq
F10.53697 (11)0.58286 (12)0.59875 (9)0.0571 (4)
F20.71216 (11)0.59357 (10)0.58733 (9)0.0483 (4)
F30.63652 (10)0.58242 (9)0.71954 (8)0.0418 (3)
F40.6204 (2)0.70674 (10)0.64035 (14)0.0853 (7)
O10.68793 (11)0.30995 (9)0.80019 (9)0.0301 (3)
O20.52205 (11)0.12281 (9)0.58920 (8)0.0286 (3)
O30.67891 (11)0.00380 (9)0.84489 (9)0.0300 (3)
B10.6263 (2)0.6169 (2)0.6367 (2)0.0302 (5)
C10.62937 (14)0.14304 (12)0.74483 (12)0.0240 (4)
C20.60645 (14)0.21643 (13)0.69395 (12)0.0247 (4)
C30.63884 (14)0.30015 (13)0.72109 (12)0.0264 (4)
C40.6192 (2)0.37264 (13)0.67007 (14)0.0305 (4)
H40.64110.42850.68690.037*
C50.5656 (2)0.35974 (13)0.59238 (13)0.0307 (5)
H50.55140.40860.55800.037*
C60.5321 (2)0.27747 (14)0.56355 (13)0.0293 (4)
H60.49670.27140.51120.035*
C70.55303 (15)0.20557 (13)0.61505 (12)0.0261 (4)
C80.60070 (14)0.05953 (13)0.71712 (12)0.0243 (4)
C90.54533 (15)0.05006 (13)0.63893 (12)0.0259 (4)
C100.5149 (2)0.03224 (14)0.61179 (13)0.0307 (5)
H100.47560.03950.56160.037*
C110.5448 (2)0.10424 (13)0.66169 (14)0.0314 (5)
H110.52640.16010.64240.038*
C120.6006 (2)0.09739 (13)0.73885 (14)0.0305 (5)
H120.61950.14720.77020.037*
C130.62709 (14)0.01423 (13)0.76747 (12)0.0267 (4)
C140.68214 (14)0.15331 (13)0.82334 (12)0.0259 (4)
C150.70531 (15)0.07872 (14)0.87366 (13)0.0283 (4)
C160.7550 (2)0.0885 (2)0.95264 (13)0.0340 (5)
H160.77110.04000.98700.041*
C170.7800 (2)0.1737 (2)0.97895 (13)0.0373 (5)
H170.81250.18081.03250.045*
C180.7594 (2)0.2488 (2)0.93008 (13)0.0337 (5)
H180.77820.30440.94990.040*
C190.71009 (15)0.23784 (14)0.85112 (12)0.0279 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0356 (7)0.0934 (12)0.0424 (8)0.0078 (8)0.0117 (6)0.0125 (8)
F20.0386 (7)0.0632 (9)0.0430 (8)0.0050 (7)0.0037 (6)0.0017 (7)
F30.0446 (8)0.0503 (8)0.0306 (6)0.0112 (6)0.0075 (6)0.0073 (6)
F40.130 (2)0.0245 (8)0.1011 (15)0.0137 (9)0.0267 (13)0.0071 (8)
O10.0288 (7)0.0320 (8)0.0296 (7)0.0031 (6)0.0012 (6)0.0057 (6)
O20.0343 (8)0.0283 (7)0.0233 (7)0.0029 (6)0.0038 (6)0.0004 (6)
O30.0284 (7)0.0337 (8)0.0279 (7)0.0039 (6)0.0010 (6)0.0036 (6)
B10.0313 (12)0.0271 (11)0.0324 (12)0.0005 (9)0.0001 (10)0.0054 (9)
C10.0194 (9)0.0294 (10)0.0233 (9)0.0017 (7)0.0034 (7)0.0021 (8)
C20.0227 (9)0.0268 (10)0.0244 (9)0.0011 (7)0.0027 (7)0.0015 (8)
C30.0218 (9)0.0311 (10)0.0262 (9)0.0004 (8)0.0031 (7)0.0043 (8)
C40.0290 (10)0.0269 (10)0.0356 (11)0.0007 (8)0.0069 (9)0.0024 (9)
C50.0302 (10)0.0296 (11)0.0323 (11)0.0033 (8)0.0060 (8)0.0048 (9)
C60.0281 (10)0.0347 (11)0.0252 (9)0.0016 (8)0.0018 (8)0.0027 (8)
C70.0245 (9)0.0299 (10)0.0238 (9)0.0019 (8)0.0026 (7)0.0036 (8)
C80.0222 (9)0.0274 (10)0.0233 (9)0.0015 (7)0.0043 (7)0.0012 (8)
C90.0275 (10)0.0275 (10)0.0226 (9)0.0010 (8)0.0045 (8)0.0017 (8)
C100.0329 (11)0.0348 (11)0.0243 (9)0.0040 (9)0.0036 (8)0.0045 (8)
C110.0331 (11)0.0272 (10)0.0340 (11)0.0036 (9)0.0111 (9)0.0056 (9)
C120.0274 (10)0.0281 (10)0.0359 (11)0.0042 (8)0.0076 (8)0.0028 (9)
C130.0213 (9)0.0323 (11)0.0265 (10)0.0034 (8)0.0051 (8)0.0010 (8)
C140.0188 (9)0.0348 (11)0.0242 (9)0.0009 (8)0.0017 (7)0.0017 (8)
C150.0211 (9)0.0378 (11)0.0260 (9)0.0017 (8)0.0032 (8)0.0004 (8)
C160.0253 (10)0.0498 (13)0.0270 (10)0.0037 (9)0.0000 (8)0.0049 (9)
C170.0251 (10)0.0625 (15)0.0245 (10)0.0032 (10)0.0032 (8)0.0022 (10)
C180.0257 (10)0.0461 (12)0.0293 (10)0.0047 (9)0.0001 (8)0.0073 (9)
C190.0214 (9)0.0359 (11)0.0265 (9)0.0006 (8)0.0027 (8)0.0023 (8)
Geometric parameters (Å, º) top
F1—B11.386 (3)C4—C51.394 (3)
F2—B11.384 (3)C5—C61.394 (3)
F3—B11.385 (3)C6—C71.376 (3)
F4—B11.369 (3)C8—C131.404 (3)
O1—C191.377 (2)C8—C91.405 (3)
O1—C31.379 (2)C9—C101.375 (3)
O2—C91.377 (2)C10—C111.391 (3)
O2—C71.378 (2)C11—C121.391 (3)
O3—C151.372 (3)C12—C131.381 (3)
O3—C131.374 (2)C14—C191.400 (3)
C1—C81.388 (3)C14—C151.405 (3)
C1—C141.394 (3)C15—C161.380 (3)
C1—C21.394 (3)C16—C171.395 (3)
C2—C31.402 (3)C17—C181.392 (3)
C2—C71.404 (3)C18—C191.380 (3)
C3—C41.376 (3)
C19—O1—C3120.7 (2)C1—C8—C13119.8 (2)
C9—O2—C7120.64 (15)C1—C8—C9119.4 (2)
C15—O3—C13120.3 (2)C13—C8—C9120.9 (2)
F4—B1—F2108.8 (2)C10—C9—O2120.0 (2)
F4—B1—F3110.2 (2)C10—C9—C8119.8 (2)
F2—B1—F3109.5 (2)O2—C9—C8120.2 (2)
F4—B1—F1110.1 (2)C9—C10—C11118.0 (2)
F2—B1—F1109.2 (2)C10—C11—C12123.7 (2)
F3—B1—F1109.0 (2)C13—C12—C11117.9 (2)
C8—C1—C14119.8 (2)O3—C13—C12120.1 (2)
C8—C1—C2120.2 (2)O3—C13—C8120.2 (2)
C14—C1—C2120.0 (2)C12—C13—C8119.7 (2)
C1—C2—C3119.7 (2)C1—C14—C19119.5 (2)
C1—C2—C7119.7 (2)C1—C14—C15119.4 (2)
C3—C2—C7120.6 (2)C19—C14—C15121.2 (2)
C4—C3—O1120.1 (2)O3—C15—C16119.7 (2)
C4—C3—C2120.2 (2)O3—C15—C14120.5 (2)
O1—C3—C2119.8 (2)C16—C15—C14119.8 (2)
C3—C4—C5117.9 (2)C15—C16—C17117.5 (2)
C6—C5—C4123.5 (2)C18—C17—C16124.1 (2)
C7—C6—C5117.9 (2)C19—C18—C17117.6 (2)
C6—C7—O2120.1 (2)O1—C19—C18120.0 (2)
C6—C7—C2120.0 (2)O1—C19—C14120.2 (2)
O2—C7—C2119.9 (2)C18—C19—C14119.8 (2)
(5) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluoroarsenate top
Crystal data top
C19H9O3·AsF6Z = 16
Mr = 474.18F(000) = 3744
Orthorhombic, PbcaDx = 1.827 Mg m3
Hall symbol: -P 2ac 2abMo Kα radiation, λ = 0.71073 Å
a = 13.550 (3) ŵ = 2.05 mm1
b = 15.807 (3) ÅT = 293 K
c = 32.201 (6) ÅPlate, orange
V = 6897 (2) Å30.30 × 0.23 × 0.18 mm
Data collection top
Siemens SMART CCD
diffractometer
7003 independent reflections
Radiation source: fine-focus sealed tube4567 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ω scan, frame data integrationθmax = 26.3°, θmin = 1.3°
Absorption correction: empirical (using intensity measurements)h = 1616
Tmin = 0.404, Tmax = 0.603k = 1919
69140 measured reflectionsl = 4040
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H atoms treated by a mixture of independent and constrained refinement
S = 1.07Calculated w = 1/[σ2(Fo2) + (0.0824P)2 + 14.1168P]
where P = (Fo2 + 2Fc2)/3
7000 reflections(Δ/σ)max = 0.376
523 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 0.97 e Å3
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
xyzUiso*/Ueq
As10.60399 (4)0.22916 (3)0.31861 (2)0.0437 (2)
F10.5238 (3)0.3152 (2)0.31736 (13)0.0792 (11)
F20.6881 (3)0.1470 (3)0.31872 (14)0.0949 (14)
F30.5041 (3)0.1599 (3)0.32144 (14)0.0912 (13)
F40.7005 (3)0.2992 (3)0.31359 (14)0.0941 (13)
F50.5989 (3)0.2223 (3)0.26548 (12)0.0956 (14)
F60.6123 (3)0.2389 (3)0.37213 (12)0.0969 (14)
As20.39514 (4)0.03844 (3)0.43634 (2)0.0498 (2)
F70.3975 (12)0.1003 (6)0.4764 (3)0.334 (9)
F80.3493 (4)0.0378 (3)0.4681 (2)0.149 (3)
F90.5065 (5)0.0003 (8)0.4437 (3)0.278 (7)
F100.4375 (5)0.1167 (4)0.4051 (2)0.165 (3)
F110.3951 (9)0.0211 (6)0.3967 (3)0.275 (6)
F120.2850 (5)0.0754 (6)0.4286 (3)0.244 (6)
O10.2888 (3)0.1032 (3)0.2914 (2)0.0763 (14)
O20.3340 (3)0.4058 (3)0.28354 (14)0.0694 (12)
O30.4597 (3)0.2254 (2)0.17558 (12)0.0591 (11)
C10.3605 (4)0.2449 (4)0.2502 (2)0.0462 (12)
C20.3097 (4)0.2547 (4)0.2877 (2)0.0567 (15)
C30.2751 (4)0.1818 (6)0.3080 (2)0.073 (2)
C40.2282 (6)0.1925 (8)0.3464 (3)0.100 (3)
H40.20450.14610.36100.119*
C50.2179 (7)0.2734 (9)0.3619 (3)0.114 (4)
H50.18680.27980.38750.137*
C60.2511 (6)0.3465 (6)0.3417 (3)0.096 (3)
H60.24210.40000.35320.115*
C70.2981 (4)0.3353 (5)0.3039 (2)0.066 (2)
C80.3967 (4)0.3158 (3)0.2296 (2)0.0451 (12)
C90.3828 (4)0.3965 (4)0.2467 (2)0.0560 (15)
C100.4167 (5)0.4664 (4)0.2249 (2)0.069 (2)
H100.40660.52070.23500.083*
C110.4652 (5)0.4541 (4)0.1882 (2)0.070 (2)
H110.48920.50120.17420.084*
C120.4806 (5)0.3744 (4)0.1706 (2)0.064 (2)
H120.51320.36850.14530.076*
C130.4464 (4)0.3053 (3)0.1917 (2)0.0484 (13)
C140.3748 (4)0.1648 (4)0.2338 (2)0.0498 (13)
C150.4250 (5)0.1551 (4)0.1964 (2)0.0559 (14)
C160.4380 (6)0.0761 (4)0.1792 (2)0.073 (2)
H160.47030.06890.15400.088*
C170.4013 (6)0.0085 (4)0.2009 (3)0.083 (2)
H170.41060.04510.18980.100*
C180.3520 (6)0.0143 (4)0.2378 (3)0.080 (2)
H180.32860.03390.25120.096*
C190.3375 (4)0.0941 (4)0.2549 (2)0.059 (2)
O40.1946 (3)0.1254 (3)0.52441 (13)0.0583 (10)
O50.1788 (3)0.1755 (3)0.54636 (13)0.0678 (12)
O60.0359 (3)0.0532 (2)0.42312 (12)0.0561 (10)
C200.1374 (4)0.0342 (3)0.4978 (2)0.0431 (12)
C210.1871 (4)0.0247 (4)0.5357 (2)0.0474 (13)
C220.2130 (4)0.0567 (4)0.5488 (2)0.0571 (15)
C230.2571 (6)0.0663 (5)0.5871 (2)0.078 (2)
H230.27490.11960.59670.094*
C240.2743 (6)0.0049 (7)0.6109 (2)0.092 (3)
H240.30370.00220.63680.111*
C250.2505 (6)0.0858 (6)0.5985 (2)0.086 (2)
H250.26430.13210.61530.103*
C260.2054 (5)0.0962 (4)0.5603 (2)0.062 (2)
C270.1075 (4)0.1153 (3)0.4848 (2)0.0449 (12)
C280.1280 (4)0.1858 (4)0.5097 (2)0.0560 (15)
C290.0964 (5)0.2645 (4)0.4968 (3)0.073 (2)
H290.10970.31240.51270.087*
C300.0449 (6)0.2709 (4)0.4601 (2)0.072 (2)
H300.02330.32410.45180.086*
C310.0237 (5)0.2024 (4)0.4350 (2)0.066 (2)
H310.01130.20940.41040.079*
C320.0558 (4)0.1234 (3)0.4474 (2)0.0476 (13)
C330.1168 (4)0.0358 (3)0.4735 (2)0.0422 (12)
C340.0663 (4)0.0267 (3)0.4361 (2)0.0503 (13)
C350.0475 (5)0.0956 (4)0.4118 (2)0.066 (2)
H350.01550.08970.38640.079*
C360.0770 (5)0.1739 (4)0.4258 (2)0.072 (2)
H360.06210.22100.40970.086*
C370.1275 (5)0.1861 (4)0.4625 (2)0.066 (2)
H370.14820.23980.47050.079*
C380.1466 (4)0.1165 (3)0.4871 (2)0.0495 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
As10.0423 (3)0.0421 (3)0.0466 (3)0.0021 (2)0.0044 (2)0.0035 (2)
F10.076 (3)0.048 (2)0.114 (3)0.012 (2)0.006 (2)0.004 (2)
F20.072 (3)0.094 (3)0.119 (3)0.041 (2)0.009 (2)0.001 (3)
F30.080 (3)0.065 (2)0.129 (4)0.013 (2)0.002 (2)0.001 (2)
F40.066 (3)0.099 (3)0.118 (3)0.030 (2)0.018 (2)0.018 (3)
F50.105 (3)0.133 (4)0.049 (2)0.005 (3)0.009 (2)0.003 (2)
F60.088 (3)0.145 (4)0.057 (2)0.003 (3)0.003 (2)0.015 (3)
As20.0546 (4)0.0400 (3)0.0547 (4)0.0046 (3)0.0126 (3)0.0005 (2)
F70.67 (3)0.159 (8)0.170 (8)0.142 (11)0.008 (11)0.070 (6)
F80.110 (4)0.099 (4)0.237 (7)0.024 (3)0.087 (4)0.087 (4)
F90.081 (4)0.432 (15)0.321 (12)0.020 (7)0.044 (6)0.244 (12)
F100.169 (6)0.128 (5)0.197 (6)0.004 (4)0.078 (5)0.089 (4)
F110.405 (17)0.232 (9)0.187 (8)0.089 (10)0.079 (9)0.149 (8)
F120.101 (5)0.369 (12)0.262 (9)0.103 (6)0.093 (5)0.232 (9)
O10.057 (3)0.089 (4)0.083 (3)0.013 (3)0.001 (2)0.039 (3)
O20.062 (3)0.078 (3)0.068 (3)0.029 (2)0.005 (2)0.010 (2)
O30.074 (3)0.049 (2)0.054 (2)0.005 (2)0.010 (2)0.003 (2)
C10.038 (3)0.056 (3)0.045 (3)0.001 (2)0.005 (2)0.010 (3)
C20.038 (3)0.082 (4)0.050 (3)0.011 (3)0.001 (2)0.015 (3)
C30.040 (3)0.117 (6)0.062 (4)0.002 (4)0.002 (3)0.028 (4)
C40.054 (4)0.168 (9)0.077 (5)0.001 (5)0.013 (4)0.046 (6)
C50.068 (5)0.209 (13)0.064 (5)0.029 (7)0.019 (4)0.009 (7)
C60.071 (5)0.143 (8)0.074 (5)0.035 (5)0.006 (4)0.008 (5)
C70.045 (3)0.100 (5)0.054 (3)0.023 (4)0.001 (3)0.003 (4)
C80.040 (3)0.048 (3)0.047 (3)0.002 (2)0.006 (2)0.002 (2)
C90.053 (4)0.054 (3)0.061 (4)0.012 (3)0.007 (3)0.000 (3)
C100.078 (5)0.040 (3)0.091 (5)0.008 (3)0.020 (4)0.001 (3)
C110.064 (4)0.048 (4)0.099 (5)0.005 (3)0.008 (4)0.021 (4)
C120.068 (4)0.060 (4)0.063 (4)0.006 (3)0.004 (3)0.017 (3)
C130.053 (3)0.041 (3)0.050 (3)0.002 (2)0.002 (3)0.007 (2)
C140.045 (3)0.048 (3)0.056 (3)0.008 (2)0.009 (2)0.013 (3)
C150.060 (4)0.050 (3)0.058 (3)0.001 (3)0.007 (3)0.003 (3)
C160.095 (5)0.050 (4)0.075 (4)0.004 (4)0.004 (4)0.006 (3)
C170.097 (6)0.048 (4)0.105 (6)0.005 (4)0.017 (5)0.006 (4)
C180.077 (5)0.049 (4)0.115 (6)0.021 (3)0.031 (5)0.028 (4)
C190.042 (3)0.065 (4)0.071 (4)0.013 (3)0.011 (3)0.025 (3)
O40.051 (2)0.057 (2)0.066 (3)0.006 (2)0.000 (2)0.010 (2)
O50.067 (3)0.071 (3)0.066 (3)0.002 (2)0.000 (2)0.025 (2)
O60.064 (3)0.054 (2)0.050 (2)0.001 (2)0.007 (2)0.002 (2)
C200.036 (3)0.046 (3)0.047 (3)0.001 (2)0.008 (2)0.004 (2)
C210.035 (3)0.062 (3)0.046 (3)0.001 (2)0.004 (2)0.006 (3)
C220.043 (3)0.080 (4)0.049 (3)0.007 (3)0.001 (3)0.009 (3)
C230.066 (4)0.101 (6)0.069 (4)0.016 (4)0.005 (4)0.013 (4)
C240.071 (5)0.147 (8)0.060 (4)0.015 (5)0.016 (4)0.002 (5)
C250.079 (5)0.117 (7)0.061 (4)0.007 (5)0.014 (4)0.026 (4)
C260.052 (4)0.079 (4)0.055 (4)0.004 (3)0.003 (3)0.013 (3)
C270.038 (3)0.048 (3)0.050 (3)0.000 (2)0.010 (2)0.003 (2)
C280.053 (3)0.052 (3)0.063 (4)0.005 (3)0.016 (3)0.011 (3)
C290.078 (5)0.043 (3)0.098 (5)0.007 (3)0.020 (4)0.014 (3)
C300.079 (5)0.047 (4)0.091 (5)0.005 (3)0.014 (4)0.015 (4)
C310.073 (4)0.057 (4)0.067 (4)0.003 (3)0.010 (3)0.016 (3)
C320.049 (3)0.041 (3)0.052 (3)0.003 (2)0.010 (3)0.007 (2)
C330.037 (3)0.042 (3)0.048 (3)0.003 (2)0.005 (2)0.002 (2)
C340.050 (3)0.041 (3)0.059 (3)0.005 (2)0.002 (3)0.001 (3)
C350.066 (4)0.072 (4)0.059 (4)0.010 (3)0.010 (3)0.010 (3)
C360.074 (5)0.054 (4)0.087 (5)0.008 (3)0.001 (4)0.022 (4)
C370.064 (4)0.043 (3)0.091 (5)0.001 (3)0.008 (3)0.006 (3)
C380.038 (3)0.045 (3)0.065 (4)0.001 (2)0.007 (3)0.003 (3)
Geometric parameters (Å, º) top
As1—F51.716 (4)C14—C151.391 (8)
As1—F41.721 (4)C14—C191.402 (7)
As1—F21.728 (4)C15—C161.377 (9)
As1—F61.734 (4)C16—C171.370 (10)
As1—F11.741 (3)C17—C181.366 (11)
As1—F31.744 (4)C18—C191.390 (10)
As2—F111.586 (6)O4—C221.363 (7)
As2—F71.620 (8)O4—C381.373 (7)
As2—F121.622 (6)O5—C261.379 (8)
As2—F91.646 (7)O5—C281.375 (7)
As2—F81.699 (4)O6—C321.383 (6)
As2—F101.695 (5)O6—C341.391 (6)
O1—C191.357 (8)C20—C331.384 (7)
O1—C31.365 (9)C20—C271.409 (7)
O2—C91.367 (7)C20—C211.401 (7)
O2—C71.381 (8)C21—C221.400 (8)
O3—C151.380 (7)C21—C261.402 (8)
O3—C131.378 (6)C22—C231.378 (9)
C1—C21.399 (8)C23—C241.381 (11)
C1—C141.386 (8)C24—C251.379 (12)
C1—C81.391 (7)C25—C261.384 (9)
C2—C71.385 (9)C27—C321.399 (8)
C2—C31.405 (9)C27—C281.402 (8)
C3—C41.399 (11)C28—C291.380 (9)
C4—C51.381 (14)C29—C301.376 (10)
C5—C61.399 (13)C30—C311.381 (9)
C6—C71.387 (10)C31—C321.381 (8)
C8—C91.402 (8)C33—C381.408 (7)
C8—C131.403 (7)C33—C341.393 (8)
C9—C101.387 (9)C34—C351.365 (8)
C10—C111.364 (10)C35—C361.377 (9)
C11—C121.397 (9)C36—C371.380 (10)
C12—C131.368 (8)C37—C381.380 (8)
F5—As1—F488.7 (2)O3—C13—C12120.0 (5)
F5—As1—F288.9 (2)O3—C13—C8119.9 (5)
F4—As1—F289.0 (2)C12—C13—C8120.1 (5)
F5—As1—F6177.9 (2)C1—C14—C15119.9 (5)
F4—As1—F689.3 (2)C1—C14—C19119.5 (6)
F2—As1—F691.3 (2)C15—C14—C19120.6 (6)
F5—As1—F190.1 (2)C16—C15—O3119.4 (6)
F4—As1—F188.2 (2)C16—C15—C14120.7 (6)
F2—As1—F1177.1 (2)O3—C15—C14119.9 (5)
F6—As1—F189.6 (2)C15—C16—C17117.1 (7)
F5—As1—F388.9 (2)C18—C17—C16124.7 (7)
F4—As1—F3177.3 (2)C17—C18—C19118.3 (6)
F2—As1—F392.3 (2)O1—C19—C18120.5 (6)
F6—As1—F393.1 (2)O1—C19—C14120.8 (6)
F1—As1—F390.4 (2)C18—C19—C14118.7 (6)
F11—As2—F7178.7 (6)C22—O4—C38120.6 (4)
F11—As2—F1295.1 (6)C26—O5—C28121.1 (5)
F7—As2—F1285.6 (6)C32—O6—C34120.1 (4)
F11—As2—F984.0 (6)C33—C20—C27120.0 (5)
F7—As2—F995.3 (7)C33—C20—C21120.3 (5)
F12—As2—F9179.1 (6)C27—C20—C21119.7 (5)
F11—As2—F893.7 (5)C22—C21—C26121.8 (5)
F7—As2—F887.4 (4)C22—C21—C20118.8 (5)
F12—As2—F890.7 (3)C26—C21—C20119.3 (5)
F9—As2—F889.1 (3)O4—C22—C23120.5 (6)
F11—As2—F1087.4 (5)O4—C22—C21120.8 (5)
F7—As2—F1091.5 (4)C23—C22—C21118.7 (6)
F12—As2—F1087.5 (3)C22—C23—C24118.7 (7)
F9—As2—F1092.7 (4)C25—C24—C23123.7 (7)
F8—As2—F10178.0 (3)C24—C25—C26118.1 (7)
C19—O1—C3120.1 (5)O5—C26—C25120.8 (6)
C9—O2—C7119.7 (5)O5—C26—C21120.2 (5)
C15—O3—C13120.7 (4)C25—C26—C21119.0 (7)
C2—C1—C14120.0 (5)C32—C27—C28121.4 (5)
C2—C1—C8119.7 (5)C32—C27—C20119.0 (5)
C14—C1—C8120.3 (5)C28—C27—C20119.6 (5)
C7—C2—C1118.9 (6)C29—C28—O5121.3 (6)
C7—C2—C3122.7 (6)C29—C28—C27118.9 (6)
C1—C2—C3118.4 (6)O5—C28—C27119.8 (5)
O1—C3—C4121.1 (8)C30—C29—C28118.8 (6)
O1—C3—C2121.3 (6)C31—C30—C29123.4 (6)
C4—C3—C2117.6 (8)C30—C31—C32118.4 (6)
C5—C4—C3118.5 (8)O6—C32—C31120.2 (5)
C4—C5—C6124.3 (8)O6—C32—C27120.6 (5)
C5—C6—C7116.8 (8)C31—C32—C27119.2 (5)
C2—C7—O2121.6 (5)C20—C33—C38119.3 (5)
C2—C7—C6120.0 (7)C20—C33—C34120.4 (5)
O2—C7—C6118.4 (7)C38—C33—C34120.2 (5)
C9—C8—C1119.9 (5)C35—C34—O6119.8 (5)
C9—C8—C13120.8 (5)C35—C34—C33120.3 (5)
C1—C8—C13119.2 (5)O6—C34—C33119.9 (5)
O2—C9—C10121.0 (6)C34—C35—C36118.4 (6)
O2—C9—C8120.2 (5)C37—C36—C35123.4 (6)
C10—C9—C8118.8 (6)C38—C37—C36118.2 (6)
C11—C10—C9118.9 (6)C37—C38—O4120.6 (5)
C10—C11—C12123.5 (6)C37—C38—C33119.4 (6)
C13—C12—C11117.9 (6)O4—C38—C33120.1 (5)
(6120K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.757 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.26 mm1
a = 12.946 (2) ÅT = 120 K
c = 16.806 (3) ÅPrism, orange
V = 2439.4 (7) Å30.25 × 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 tubeRint = 0.042
Graphite monochromatorθmax = 26.3°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8019 measured reflectionsk = 1616
557 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.05Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
557 reflections(Δ/σ)max = 0.002
47 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0213 (3)
F10.04986 (8)0.11667 (8)0.05520 (5)0.0319 (3)
O10.78471 (10)0.00000.25000.0267 (4)
C11.00000.00000.25000.0202 (7)
C21.00000.10771 (15)0.25000.0221 (4)
C30.89117 (12)0.10668 (12)0.25162 (7)0.0241 (4)
C40.89034 (14)0.21302 (14)0.25388 (8)0.0299 (4)
H40.81930.21420.25780.036*
C51.00000.3184 (2)0.25000.0322 (5)
H51.00000.39030.25000.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0200 (3)0.0200 (3)0.0239 (4)0.0100 (2)0.0000.000
F10.0322 (5)0.0258 (5)0.0363 (5)0.0134 (4)0.0033 (4)0.0081 (4)
O10.0231 (5)0.0318 (8)0.0280 (7)0.0159 (4)0.0008 (3)0.0016 (6)
C10.0226 (10)0.0226 (10)0.0152 (14)0.0113 (5)0.0000.000
C20.0262 (10)0.0245 (8)0.0161 (8)0.0131 (5)0.0010 (7)0.0005 (4)
C30.0280 (8)0.0272 (8)0.0190 (6)0.0153 (7)0.0005 (5)0.0006 (5)
C40.0401 (9)0.0371 (9)0.0233 (7)0.0273 (8)0.0028 (6)0.0022 (6)
C50.0528 (14)0.0280 (7)0.0239 (9)0.0264 (7)0.0052 (9)0.0026 (5)
Geometric parameters (Å, º) top
P1—F1i1.6074 (8)C1—C2vii1.394 (2)
P1—F11.6074 (8)C1—C2viii1.394 (2)
P1—F1ii1.6074 (8)C1—C21.394 (2)
P1—F1iii1.6074 (8)C2—C3ix1.403 (2)
P1—F1iv1.6074 (8)C2—C31.403 (2)
P1—F1v1.6074 (8)C3—C41.383 (2)
O1—C31.380 (2)C4—C51.395 (2)
O1—C3vi1.380 (2)C5—C4ix1.395 (2)
F1i—P1—F1180.0F1iv—P1—F1v90.02 (5)
F1i—P1—F1ii89.98 (5)C3—O1—C3vi120.22 (15)
F1—P1—F1ii90.02 (5)C2vii—C1—C2viii120.0
F1i—P1—F1iii89.98 (5)C2vii—C1—C2120.0
F1—P1—F1iii90.02 (5)C2viii—C1—C2120.0
F1ii—P1—F1iii90.02 (5)C1—C2—C3ix119.52 (9)
F1i—P1—F1iv90.02 (5)C1—C2—C3119.52 (9)
F1—P1—F1iv89.98 (5)C3ix—C2—C3121.0 (2)
F1ii—P1—F1iv89.98 (5)O1—C3—C4119.74 (13)
F1iii—P1—F1iv180.0O1—C3—C2120.33 (13)
F1i—P1—F1v90.02 (5)C4—C3—C2119.93 (15)
F1—P1—F1v89.98 (5)C3—C4—C5117.54 (14)
F1ii—P1—F1v180.0C4—C5—C4ix124.0 (2)
F1iii—P1—F1v89.98 (5)
Symmetry codes: (i) x, y, z; (ii) y, xy, z; (iii) x+y, x, z; (iv) xy, x, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(7) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium nitratehydrogennitrate top
Crystal data top
C19H10N2O9·HNO3·NO3Z = 4
Mr = 410.29F(000) = 840
Monoclinic, P21/nDx = 1.660 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 6.4960 (13) ŵ = 0.14 mm1
b = 7.6530 (15) ÅT = 120 K
c = 33.039 (7) ÅPlate, 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 tube2173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 8.192 pixels mm-1θmax = 26.3°, θmin = 1.2°
ω scan, frame data integrationh = 88
Absorption correction: empirical (using intensity measurements)k = 99
Tmin = 0.776, Tmax = 0.980l = 4141
17025 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.00Calculated w = 1/[σ2(Fo2) + (0.0549P)2 + 0.5233P]
where P = (Fo2 + 2Fc2)/3
3345 reflections(Δ/σ)max = 0.002
271 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.7353 (2)0.89044 (19)0.16804 (4)0.0197 (4)
O20.2733 (2)1.00261 (19)0.05309 (4)0.0209 (4)
O30.1106 (2)1.22049 (19)0.18556 (4)0.0216 (4)
C10.3724 (3)1.0371 (3)0.13560 (6)0.0163 (5)
C20.5040 (3)0.9468 (3)0.11042 (6)0.0164 (5)
C30.6851 (3)0.8702 (3)0.12728 (6)0.0175 (5)
C40.8125 (3)0.7748 (3)0.10320 (7)0.0213 (5)
H40.93140.72230.11390.026*
C50.7569 (4)0.7596 (3)0.06216 (7)0.0237 (5)
H50.84220.69530.04570.028*
C60.5798 (4)0.8359 (3)0.04435 (7)0.0224 (5)
H60.54920.82440.01680.027*
C70.4524 (3)0.9288 (3)0.06910 (6)0.0179 (5)
C80.1912 (3)1.1098 (3)0.11928 (6)0.0182 (5)
C90.1438 (3)1.0947 (3)0.07770 (6)0.0192 (5)
C100.0301 (3)1.1744 (3)0.06117 (7)0.0235 (5)
H100.06311.16660.03360.028*
C110.1544 (4)1.2668 (3)0.08711 (7)0.0251 (5)
H110.27181.32050.07610.030*
C120.1141 (3)1.2843 (3)0.12880 (7)0.0242 (5)
H120.20171.34700.14510.029*
C130.0611 (3)1.2045 (3)0.14470 (6)0.0192 (5)
C140.4229 (3)1.0553 (3)0.17675 (6)0.0171 (5)
C150.2893 (3)1.1470 (3)0.20178 (6)0.0193 (5)
C160.3357 (4)1.1634 (3)0.24261 (7)0.0246 (5)
H160.24791.22170.25970.029*
C170.5194 (4)1.0892 (3)0.25738 (7)0.0247 (5)
H170.55231.10060.28490.030*
C180.6572 (4)0.9988 (3)0.23348 (7)0.0231 (5)
H180.77850.95210.24460.028*
C190.6070 (3)0.9813 (3)0.19297 (7)0.0188 (5)
N10.2727 (3)0.5112 (2)0.03952 (6)0.0213 (4)
O40.2160 (2)0.58203 (19)0.07456 (4)0.0230 (4)
H4A0.27010.52810.09350.035*0.50
O50.3911 (2)0.3865 (2)0.04094 (5)0.0268 (4)
O60.1997 (3)0.5790 (2)0.00891 (5)0.0307 (4)
N20.4074 (3)0.5514 (2)0.16270 (6)0.0216 (4)
O70.2678 (3)0.6628 (2)0.16200 (5)0.0276 (4)
O80.5267 (3)0.5279 (2)0.19189 (5)0.0353 (5)
O90.4293 (2)0.45440 (19)0.13082 (5)0.0250 (4)
H90.39570.35370.13590.038*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0199 (8)0.0211 (8)0.0180 (8)0.0043 (6)0.0003 (6)0.0006 (6)
O20.0225 (9)0.0213 (8)0.0187 (8)0.0001 (7)0.0024 (7)0.0001 (6)
O30.0200 (9)0.0250 (8)0.0199 (8)0.0040 (7)0.0025 (7)0.0004 (6)
C10.0178 (12)0.0124 (10)0.0189 (12)0.0039 (8)0.0020 (9)0.0021 (8)
C20.0167 (11)0.0145 (11)0.0179 (11)0.0025 (8)0.0002 (9)0.0003 (8)
C30.0196 (12)0.0169 (11)0.0162 (11)0.0025 (9)0.0014 (9)0.0015 (9)
C40.0214 (13)0.0174 (11)0.0251 (13)0.0012 (9)0.0019 (10)0.0009 (9)
C50.0234 (13)0.0187 (11)0.0295 (14)0.0008 (9)0.0086 (10)0.0040 (10)
C60.0275 (13)0.0211 (12)0.0188 (12)0.0046 (10)0.0034 (10)0.0018 (9)
C70.0166 (12)0.0161 (11)0.0208 (12)0.0039 (9)0.0011 (9)0.0014 (9)
C80.0168 (11)0.0174 (11)0.0204 (12)0.0030 (9)0.0000 (9)0.0030 (9)
C90.0185 (12)0.0169 (11)0.0223 (12)0.0045 (9)0.0005 (9)0.0012 (9)
C100.0239 (13)0.0227 (12)0.0234 (12)0.0055 (10)0.0054 (10)0.0041 (10)
C110.0179 (12)0.0236 (13)0.0335 (14)0.0015 (9)0.0045 (11)0.0062 (10)
C120.0176 (12)0.0203 (12)0.0350 (14)0.0004 (9)0.0047 (10)0.0031 (10)
C130.0182 (12)0.0166 (11)0.0230 (12)0.0031 (9)0.0008 (10)0.0019 (9)
C140.0183 (12)0.0168 (11)0.0164 (11)0.0032 (9)0.0016 (9)0.0014 (9)
C150.0203 (12)0.0175 (11)0.0202 (12)0.0009 (9)0.0013 (9)0.0011 (9)
C160.0318 (14)0.0214 (12)0.0209 (12)0.0021 (10)0.0073 (10)0.0018 (9)
C170.0335 (14)0.0248 (12)0.0155 (11)0.0041 (11)0.0008 (10)0.0004 (9)
C180.0267 (13)0.0216 (11)0.0208 (12)0.0014 (10)0.0038 (10)0.0010 (9)
C190.0201 (12)0.0161 (11)0.0201 (12)0.0006 (9)0.0018 (9)0.0009 (9)
N10.0176 (10)0.0249 (10)0.0216 (11)0.0039 (8)0.0021 (8)0.0031 (8)
O40.0242 (9)0.0267 (8)0.0182 (8)0.0056 (7)0.0016 (7)0.0032 (7)
O50.0262 (9)0.0242 (9)0.0301 (10)0.0060 (7)0.0033 (7)0.0055 (7)
O60.0326 (10)0.0381 (10)0.0212 (9)0.0016 (8)0.0048 (8)0.0039 (7)
N20.0245 (11)0.0205 (10)0.0199 (10)0.0056 (8)0.0022 (9)0.0019 (8)
O70.0365 (10)0.0242 (9)0.0223 (9)0.0066 (8)0.0045 (7)0.0002 (7)
O80.0343 (11)0.0475 (11)0.0234 (10)0.0017 (8)0.0106 (8)0.0009 (8)
O90.0270 (9)0.0231 (8)0.0248 (9)0.0017 (7)0.0013 (7)0.0040 (7)
Geometric parameters (Å, º) top
O1—C191.380 (3)C9—C101.381 (3)
O1—C31.383 (2)C10—C111.390 (3)
O2—C91.382 (3)C11—C121.400 (3)
O2—C71.382 (3)C12—C131.379 (3)
O3—C151.381 (3)C14—C151.407 (3)
O3—C131.382 (3)C14—C191.412 (3)
C1—C81.394 (3)C15—C161.378 (3)
C1—C141.395 (3)C16—C171.395 (3)
C1—C21.396 (3)C17—C181.397 (3)
C2—C71.401 (3)C18—C191.373 (3)
C2—C31.412 (3)N1—O61.218 (2)
C3—C41.376 (3)N1—O51.226 (2)
C4—C51.396 (3)N1—O41.341 (2)
C5—C61.402 (3)N2—O81.230 (2)
C6—C71.380 (3)N2—O71.244 (2)
C8—C91.402 (3)N2—O91.300 (2)
C8—C131.412 (3)
C19—O1—C3120.69 (16)C9—C10—C11117.8 (2)
C9—O2—C7120.29 (16)C10—C11—C12124.2 (2)
C15—O3—C13120.49 (17)C13—C12—C11117.2 (2)
C8—C1—C14120.3 (2)C12—C13—O3119.6 (2)
C8—C1—C2119.56 (19)C12—C13—C8120.2 (2)
C14—C1—C2120.11 (19)O3—C13—C8120.15 (19)
C1—C2—C7119.88 (19)C1—C14—C15119.6 (2)
C1—C2—C3119.30 (19)C1—C14—C19119.9 (2)
C7—C2—C3120.80 (19)C15—C14—C19120.56 (19)
C4—C3—O1119.71 (19)C16—C15—O3119.7 (2)
C4—C3—C2120.08 (19)C16—C15—C14120.1 (2)
O1—C3—C2120.21 (18)O3—C15—C14120.15 (19)
C3—C4—C5117.7 (2)C15—C16—C17117.5 (2)
C4—C5—C6123.7 (2)C16—C17—C18124.1 (2)
C7—C6—C5117.8 (2)C19—C18—C17117.6 (2)
C6—C7—O2119.86 (19)C18—C19—O1120.18 (19)
C6—C7—C2120.0 (2)C18—C19—C14120.0 (2)
O2—C7—C2120.18 (19)O1—C19—C14119.77 (18)
C1—C8—C9120.0 (2)O6—N1—O5126.13 (19)
C1—C8—C13119.30 (19)O6—N1—O4115.70 (18)
C9—C8—C13120.6 (2)O5—N1—O4118.17 (18)
C10—C9—O2119.94 (19)O8—N2—O7123.66 (19)
C10—C9—C8120.0 (2)O8—N2—O9117.93 (19)
O2—C9—C8120.05 (19)O7—N2—O9118.41 (18)
(8) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium trifluoromethanesulphonate top
Crystal data top
C19H9O3·CF3O3SZ = 8
Mr = 434.33F(000) = 1760
Monoclinic, P21/cDx = 1.711 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.771 (3) ŵ = 0.27 mm1
b = 15.473 (3) ÅT = 120 K
c = 15.332 (3) ÅPlate, 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 tube5770 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scan, frame data integrationθmax = 26.3°, θmin = 1.4°
Absorption correction: empirical (using intensity measurements)h = 1919
Tmin = 0.776, Tmax = 0.980k = 1919
35210 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0524P)2 + 1.1788P]
where P = (Fo2 + 2Fc2)/3
6860 reflections(Δ/σ)max = 0.002
541 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.54 e Å3
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
xyzUiso*/Ueq
S10.04323 (2)0.33597 (2)0.34450 (2)0.01593 (9)
F10.03354 (7)0.39911 (7)0.49895 (7)0.0348 (2)
F20.17308 (6)0.40083 (7)0.50603 (7)0.0335 (2)
F30.06916 (7)0.49326 (6)0.41656 (7)0.0345 (2)
O70.09944 (7)0.36086 (7)0.29540 (8)0.0228 (2)
O80.06597 (8)0.25271 (7)0.39159 (8)0.0268 (3)
O90.05613 (7)0.35477 (7)0.29248 (8)0.0241 (2)
C390.08176 (11)0.41085 (10)0.44655 (11)0.0219 (3)
S20.49800 (3)0.62201 (2)0.21757 (3)0.02098 (10)
F40.35412 (7)0.53216 (7)0.09460 (7)0.0329 (2)
F50.38414 (8)0.64883 (8)0.03540 (8)0.0444 (3)
F60.47308 (9)0.53659 (9)0.06091 (10)0.0561 (4)
O100.56353 (8)0.67735 (7)0.20111 (9)0.0305 (3)
O110.43225 (9)0.66602 (7)0.24429 (9)0.0296 (3)
O120.53778 (10)0.54445 (8)0.27151 (10)0.0451 (4)
C400.42377 (12)0.58286 (11)0.09589 (12)0.0272 (4)
O10.02209 (7)0.67067 (7)0.30620 (7)0.0199 (2)
O20.11471 (7)0.46579 (7)0.12605 (7)0.0216 (2)
O30.19868 (7)0.45498 (7)0.10766 (7)0.0213 (2)
C10.02069 (10)0.53023 (9)0.18029 (10)0.0172 (3)
C20.06860 (10)0.56772 (9)0.21666 (10)0.0175 (3)
C30.08880 (10)0.63931 (10)0.27893 (10)0.0190 (3)
C40.17619 (11)0.67793 (10)0.31357 (11)0.0233 (3)
H40.19060.72570.35440.028*
C50.24243 (11)0.64320 (11)0.28554 (12)0.0246 (3)
H50.30140.66910.30880.029*
C60.22497 (11)0.57175 (10)0.22458 (11)0.0231 (3)
H60.27110.55010.20810.028*
C70.13662 (10)0.53421 (10)0.18951 (10)0.0196 (3)
C80.04223 (10)0.46058 (10)0.11644 (10)0.0187 (3)
C90.02676 (10)0.42856 (10)0.08996 (10)0.0201 (3)
C100.00572 (12)0.36032 (10)0.02617 (11)0.0246 (3)
H100.05010.33880.00710.030*
C110.08413 (12)0.32448 (10)0.00885 (11)0.0266 (3)
H110.09840.27830.05170.032*
C120.15383 (12)0.35412 (10)0.01690 (11)0.0246 (3)
H120.21290.32840.00790.030*
C130.13211 (11)0.42298 (10)0.08041 (10)0.0202 (3)
C140.08840 (10)0.56311 (9)0.20675 (10)0.0176 (3)
C150.17839 (10)0.52483 (10)0.16944 (10)0.0188 (3)
C160.24617 (10)0.55783 (10)0.19418 (11)0.0225 (3)
H160.30580.53330.17060.027*
C170.22245 (11)0.62949 (11)0.25597 (11)0.0238 (3)
H170.26800.65190.27290.029*
C180.13430 (11)0.66912 (10)0.29347 (11)0.0220 (3)
H180.12150.71720.33360.026*
C190.06671 (10)0.63469 (10)0.26903 (10)0.0188 (3)
O40.43422 (8)0.66177 (7)0.85196 (8)0.0238 (2)
O50.38058 (7)0.60993 (7)0.52163 (8)0.0225 (2)
O60.69698 (7)0.64935 (7)0.76972 (8)0.0239 (2)
C200.50397 (10)0.64049 (9)0.71449 (11)0.0178 (3)
C210.40731 (10)0.63707 (9)0.68652 (11)0.0185 (3)
C220.37310 (11)0.64680 (9)0.75670 (11)0.0208 (3)
C230.27765 (12)0.64035 (10)0.73010 (13)0.0253 (3)
H230.25370.64720.77540.030*
C240.21844 (11)0.62332 (10)0.63327 (13)0.0275 (4)
H240.15420.61830.61520.033*
C250.25048 (11)0.61347 (10)0.56201 (12)0.0256 (3)
H250.20880.60260.49800.031*
C260.34606 (11)0.62040 (10)0.58955 (11)0.0207 (3)
C270.53878 (10)0.62865 (9)0.64590 (11)0.0187 (3)
C280.47626 (10)0.61349 (9)0.54864 (11)0.0199 (3)
C290.51029 (11)0.60131 (10)0.48059 (11)0.0238 (3)
H290.46970.59240.41580.029*
C300.60761 (11)0.60275 (11)0.51190 (12)0.0260 (3)
H300.63090.59330.46640.031*
C310.67215 (11)0.61756 (11)0.60794 (12)0.0252 (3)
H310.73660.61770.62620.030*
C320.63655 (10)0.63202 (10)0.67468 (11)0.0209 (3)
C330.56568 (11)0.65564 (9)0.81097 (11)0.0198 (3)
C340.66265 (11)0.66184 (10)0.83758 (11)0.0228 (3)
C350.72378 (12)0.68139 (11)0.93177 (12)0.0285 (4)
H350.78800.68730.95040.034*
C360.68603 (13)0.69196 (11)0.99826 (12)0.0301 (4)
H360.72710.70481.06200.036*
C370.59048 (13)0.68442 (11)0.97491 (12)0.0282 (4)
H370.56840.69071.02180.034*
C380.52968 (11)0.66725 (10)0.87962 (11)0.0225 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0154 (2)0.0183 (2)0.0140 (2)0.00032 (13)0.00631 (13)0.00128 (13)
F10.0382 (6)0.0494 (6)0.0224 (5)0.0042 (5)0.0185 (4)0.0022 (4)
F20.0230 (5)0.0436 (6)0.0223 (5)0.0008 (4)0.0010 (4)0.0053 (4)
F30.0464 (6)0.0208 (5)0.0291 (5)0.0004 (4)0.0098 (5)0.0027 (4)
O70.0194 (5)0.0317 (6)0.0197 (5)0.0003 (4)0.0109 (4)0.0034 (4)
O80.0371 (7)0.0201 (6)0.0215 (6)0.0007 (5)0.0111 (5)0.0046 (4)
O90.0146 (5)0.0345 (6)0.0209 (5)0.0014 (4)0.0055 (4)0.0004 (5)
C390.0222 (7)0.0246 (8)0.0178 (7)0.0009 (6)0.0075 (6)0.0006 (6)
S20.0209 (2)0.0156 (2)0.0246 (2)0.00064 (14)0.00815 (15)0.00097 (14)
F40.0297 (5)0.0358 (6)0.0334 (5)0.0137 (4)0.0138 (4)0.0075 (4)
F50.0441 (6)0.0567 (7)0.0248 (5)0.0139 (5)0.0078 (5)0.0094 (5)
F60.0645 (8)0.0584 (8)0.0717 (8)0.0213 (6)0.0543 (7)0.0395 (7)
O100.0229 (6)0.0243 (6)0.0466 (7)0.0048 (5)0.0172 (5)0.0070 (5)
O110.0375 (7)0.0266 (6)0.0350 (7)0.0030 (5)0.0254 (6)0.0062 (5)
O120.0442 (8)0.0236 (6)0.0490 (8)0.0052 (6)0.0028 (7)0.0089 (6)
C400.0287 (8)0.0306 (9)0.0282 (8)0.0064 (7)0.0181 (7)0.0067 (7)
O10.0180 (5)0.0221 (5)0.0207 (5)0.0004 (4)0.0095 (4)0.0012 (4)
O20.0223 (5)0.0238 (5)0.0214 (5)0.0047 (4)0.0121 (4)0.0016 (4)
O30.0188 (5)0.0234 (5)0.0207 (5)0.0016 (4)0.0077 (4)0.0008 (4)
C10.0198 (7)0.0176 (7)0.0136 (6)0.0032 (6)0.0066 (6)0.0072 (5)
C20.0178 (7)0.0199 (7)0.0154 (7)0.0028 (6)0.0076 (6)0.0053 (6)
C30.0181 (7)0.0215 (7)0.0180 (7)0.0039 (6)0.0084 (6)0.0052 (6)
C40.0217 (8)0.0231 (8)0.0234 (8)0.0011 (6)0.0082 (6)0.0023 (6)
C50.0159 (7)0.0287 (8)0.0277 (8)0.0006 (6)0.0082 (6)0.0075 (7)
C60.0190 (7)0.0288 (8)0.0251 (8)0.0063 (6)0.0130 (6)0.0086 (6)
C70.0215 (7)0.0208 (7)0.0174 (7)0.0045 (6)0.0094 (6)0.0056 (6)
C80.0221 (7)0.0194 (7)0.0142 (7)0.0027 (6)0.0075 (6)0.0044 (6)
C90.0225 (7)0.0219 (7)0.0157 (7)0.0045 (6)0.0081 (6)0.0064 (6)
C100.0334 (9)0.0231 (8)0.0191 (7)0.0087 (7)0.0130 (7)0.0039 (6)
C110.0386 (9)0.0201 (8)0.0194 (8)0.0037 (7)0.0109 (7)0.0006 (6)
C120.0286 (8)0.0219 (8)0.0194 (7)0.0023 (6)0.0067 (6)0.0023 (6)
C130.0236 (7)0.0207 (7)0.0165 (7)0.0027 (6)0.0089 (6)0.0052 (6)
C140.0175 (7)0.0204 (7)0.0151 (7)0.0024 (6)0.0072 (6)0.0049 (6)
C150.0200 (7)0.0193 (7)0.0158 (7)0.0013 (6)0.0064 (6)0.0044 (6)
C160.0167 (7)0.0276 (8)0.0240 (8)0.0015 (6)0.0094 (6)0.0076 (6)
C170.0220 (8)0.0285 (8)0.0258 (8)0.0074 (6)0.0150 (7)0.0077 (7)
C180.0244 (8)0.0234 (8)0.0207 (8)0.0042 (6)0.0120 (6)0.0013 (6)
C190.0179 (7)0.0211 (7)0.0170 (7)0.0011 (6)0.0072 (6)0.0044 (6)
O40.0274 (6)0.0236 (6)0.0248 (6)0.0002 (4)0.0154 (5)0.0025 (4)
O50.0166 (5)0.0279 (6)0.0225 (5)0.0024 (4)0.0080 (4)0.0025 (4)
O60.0163 (5)0.0288 (6)0.0242 (6)0.0002 (4)0.0066 (4)0.0037 (5)
C200.0192 (7)0.0113 (6)0.0227 (7)0.0004 (5)0.0089 (6)0.0026 (5)
C210.0186 (7)0.0134 (7)0.0251 (8)0.0013 (5)0.0110 (6)0.0023 (6)
C220.0247 (8)0.0132 (7)0.0269 (8)0.0012 (6)0.0135 (7)0.0031 (6)
C230.0267 (8)0.0190 (7)0.0390 (9)0.0017 (6)0.0223 (7)0.0046 (7)
C240.0192 (8)0.0229 (8)0.0435 (10)0.0011 (6)0.0165 (7)0.0061 (7)
C250.0185 (7)0.0257 (8)0.0306 (8)0.0013 (6)0.0086 (6)0.0028 (7)
C260.0196 (7)0.0176 (7)0.0262 (8)0.0003 (6)0.0113 (6)0.0013 (6)
C270.0170 (7)0.0155 (7)0.0239 (8)0.0009 (5)0.0092 (6)0.0019 (6)
C280.0163 (7)0.0173 (7)0.0255 (8)0.0005 (6)0.0085 (6)0.0004 (6)
C290.0257 (8)0.0238 (8)0.0226 (8)0.0008 (6)0.0112 (6)0.0009 (6)
C300.0284 (9)0.0253 (8)0.0320 (9)0.0023 (7)0.0203 (7)0.0019 (7)
C310.0182 (7)0.0268 (8)0.0332 (9)0.0023 (6)0.0135 (7)0.0050 (7)
C320.0180 (7)0.0191 (7)0.0237 (8)0.0011 (6)0.0075 (6)0.0044 (6)
C330.0217 (8)0.0150 (7)0.0212 (7)0.0006 (6)0.0079 (6)0.0039 (6)
C340.0229 (8)0.0197 (7)0.0238 (8)0.0010 (6)0.0082 (6)0.0055 (6)
C350.0240 (8)0.0271 (8)0.0262 (8)0.0010 (7)0.0030 (7)0.0050 (7)
C360.0374 (10)0.0242 (8)0.0194 (8)0.0019 (7)0.0038 (7)0.0029 (6)
C370.0400 (10)0.0235 (8)0.0220 (8)0.0008 (7)0.0143 (7)0.0036 (6)
C380.0282 (8)0.0163 (7)0.0250 (8)0.0006 (6)0.0134 (7)0.0046 (6)
Geometric parameters (Å, º) top
S1—O71.4422 (11)C12—C131.382 (2)
S1—O81.4439 (11)C14—C191.404 (2)
S1—O91.4464 (12)C14—C151.410 (2)
S1—C391.826 (2)C15—C161.378 (2)
F1—C391.337 (2)C16—C171.400 (2)
F2—C391.338 (2)C17—C181.395 (2)
F3—C391.341 (2)C18—C191.381 (2)
S2—O121.4380 (13)O4—C221.377 (2)
S2—O111.4405 (12)O4—C381.378 (2)
S2—O101.4462 (12)O5—C261.378 (2)
S2—C401.823 (2)O5—C281.382 (2)
F4—C401.343 (2)O6—C341.379 (2)
F5—C401.338 (2)O6—C321.378 (2)
F6—C401.329 (2)C20—C271.393 (2)
O1—C31.378 (2)C20—C211.394 (2)
O1—C191.380 (2)C20—C331.393 (2)
O2—C91.377 (2)C21—C261.402 (2)
O2—C71.377 (2)C21—C221.405 (2)
O3—C151.380 (2)C22—C231.382 (2)
O3—C131.379 (2)C23—C241.394 (3)
C1—C141.393 (2)C24—C251.397 (2)
C1—C81.395 (2)C25—C261.382 (2)
C1—C21.396 (2)C27—C321.409 (2)
C2—C71.407 (2)C27—C281.406 (2)
C2—C31.406 (2)C28—C291.378 (2)
C3—C41.380 (2)C29—C301.396 (2)
C4—C51.398 (2)C30—C311.399 (2)
C5—C61.396 (2)C31—C321.382 (2)
C6—C71.385 (2)C33—C341.405 (2)
C8—C131.405 (2)C33—C381.407 (2)
C8—C91.406 (2)C34—C351.378 (2)
C9—C101.378 (2)C35—C361.395 (3)
C10—C111.394 (2)C36—C371.395 (3)
C11—C121.397 (2)C37—C381.382 (2)
O7—S1—O8115.06 (7)C1—C14—C19119.65 (13)
O7—S1—O9115.00 (7)C1—C14—C15119.50 (14)
O8—S1—O9115.47 (7)C19—C14—C15120.85 (13)
O7—S1—C39103.08 (7)C16—C15—O3120.17 (13)
O8—S1—C39102.68 (7)C16—C15—C14119.81 (14)
O9—S1—C39102.90 (7)O3—C15—C14120.03 (13)
F1—C39—F2107.41 (12)C15—C16—C17117.92 (14)
F1—C39—F3107.27 (13)C18—C17—C16123.59 (14)
F2—C39—F3107.43 (13)C19—C18—C17117.85 (14)
F1—C39—S1111.34 (11)O1—C19—C18119.80 (14)
F2—C39—S1111.74 (11)O1—C19—C14120.22 (13)
F3—C39—S1111.40 (10)C18—C19—C14119.98 (14)
O12—S2—O11114.79 (9)C22—O4—C38120.37 (12)
O12—S2—O10115.33 (8)C26—O5—C28120.45 (12)
O11—S2—O10115.27 (7)C34—O6—C32120.49 (12)
O12—S2—C40103.74 (8)C27—C20—C21119.93 (14)
O11—S2—C40103.07 (8)C27—C20—C33120.06 (14)
O10—S2—C40102.03 (8)C21—C20—C33120.00 (14)
F6—C40—F5108.08 (14)C20—C21—C26119.47 (14)
F6—C40—F4107.29 (14)C20—C21—C22119.47 (14)
F5—C40—F4107.59 (14)C26—C21—C22121.00 (14)
F6—C40—S2111.31 (12)O4—C22—C23119.81 (14)
F5—C40—S2110.83 (12)O4—C22—C21120.38 (14)
F4—C40—S2111.55 (11)C23—C22—C21119.81 (15)
C3—O1—C19120.29 (12)C22—C23—C24117.95 (15)
C9—O2—C7120.40 (12)C23—C24—C25123.45 (15)
C15—O3—C13120.58 (12)C26—C25—C24118.0 (2)
C14—C1—C8120.16 (14)O5—C26—C25119.74 (14)
C14—C1—C2119.99 (14)O5—C26—C21120.45 (13)
C8—C1—C2119.84 (14)C25—C26—C21119.81 (15)
C1—C2—C7119.67 (14)C20—C27—C32119.64 (14)
C1—C2—C3119.40 (13)C20—C27—C28119.85 (14)
C7—C2—C3120.93 (14)C32—C27—C28120.50 (14)
C4—C3—O1119.82 (14)C29—C28—O5120.07 (14)
C4—C3—C2119.80 (14)C29—C28—C27120.12 (14)
O1—C3—C2120.37 (13)O5—C28—C27119.81 (14)
C3—C4—C5118.04 (15)C28—C29—C30117.96 (14)
C6—C5—C4123.61 (14)C29—C30—C31123.66 (15)
C7—C6—C5117.73 (14)C32—C31—C30117.52 (14)
O2—C7—C6119.92 (13)C31—C32—O6119.85 (14)
O2—C7—C2120.17 (13)C31—C32—C27120.19 (14)
C6—C7—C2119.88 (14)O6—C32—C27119.97 (14)
C1—C8—C13119.53 (14)C20—C33—C34119.41 (15)
C1—C8—C9119.42 (14)C20—C33—C38119.53 (14)
C13—C8—C9121.04 (14)C34—C33—C38121.03 (14)
O2—C9—C10119.74 (14)O6—C34—C35119.76 (14)
O2—C9—C8120.49 (13)O6—C34—C33120.36 (14)
C10—C9—C8119.76 (14)C35—C34—C33119.9 (2)
C9—C10—C11118.00 (15)C34—C35—C36117.7 (2)
C10—C11—C12123.62 (15)C37—C36—C35124.0 (2)
C13—C12—C11117.85 (15)C38—C37—C36117.7 (2)
C12—C13—O3120.09 (14)O4—C38—C37120.10 (15)
C12—C13—C8119.72 (14)O4—C38—C33120.20 (14)
O3—C13—C8120.19 (13)C37—C38—C33119.7 (2)
(9) Bis(4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium) tetradecachlorohexamolybdate top
Crystal data top
C19H9O3·Cl7Mo3Z = 8
Mr = 821.23F(000) = 3136
Monoclinic, C2/cDx = 2.392 Mg m3
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 18.205 (4) ŵ = 2.47 mm1
b = 13.540 (3) ÅT = 120 K
c = 18.679 (4) ÅPrism, 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 tube4029 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scan, frame data integrationθmax = 26.3°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements)h = 2222
Tmin = 0.776, Tmax = 0.862k = 1616
23431 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H atoms treated by a mixture of independent and constrained refinement
S = 1.09Calculated w = 1/[σ2(Fo2) + (0.031P)2 + 4.5834P]
where P = (Fo2 + 2Fc2)/3
4631 reflections(Δ/σ)max = 0.010
289 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 1.21 e Å3
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
xyzUiso*/Ueq
Mo10.050872 (12)0.519055 (16)0.421732 (11)0.00874 (6)
Mo20.088778 (12)0.522183 (16)0.441491 (11)0.00876 (6)
Mo30.007917 (12)0.366634 (16)0.478971 (11)0.00892 (6)
Cl10.11919 (4)0.54599 (5)0.32044 (3)0.01566 (14)
Cl20.20765 (3)0.55673 (5)0.36800 (3)0.01437 (13)
Cl30.02055 (4)0.19090 (5)0.45114 (4)0.01621 (14)
Cl40.02895 (3)0.66392 (5)0.38961 (3)0.01189 (13)
Cl50.13876 (3)0.37565 (5)0.49929 (3)0.01174 (13)
Cl60.12389 (3)0.36952 (4)0.46138 (3)0.01160 (13)
Cl70.04240 (3)0.41385 (5)0.35073 (3)0.01179 (13)
O10.29081 (10)0.36002 (13)0.59683 (10)0.0146 (4)
O20.37390 (11)0.66348 (14)0.69485 (10)0.0167 (4)
O30.38274 (10)0.35869 (14)0.82754 (10)0.0153 (4)
C10.35013 (14)0.4602 (2)0.70579 (14)0.0129 (5)
C20.33433 (14)0.5109 (2)0.64497 (14)0.0135 (5)
C30.30655 (14)0.4590 (2)0.58929 (14)0.0142 (6)
C40.29515 (15)0.5081 (2)0.52694 (15)0.0172 (6)
H40.27930.47440.48850.021*
C50.30814 (15)0.6098 (2)0.52334 (15)0.0177 (6)
H50.30010.64300.48160.021*
C60.33248 (15)0.6641 (2)0.57888 (15)0.0175 (6)
H60.33860.73220.57520.021*
C70.34714 (14)0.6135 (2)0.63956 (14)0.0145 (5)
C80.37924 (15)0.5109 (2)0.76055 (14)0.0127 (5)
C90.39032 (15)0.6136 (2)0.75494 (14)0.0146 (6)
C100.41693 (16)0.6648 (2)0.81001 (15)0.0191 (6)
H100.42320.73290.80780.023*
C110.43409 (16)0.6105 (2)0.86891 (15)0.0196 (6)
H110.45270.64450.90580.024*
C120.42508 (16)0.5082 (2)0.87612 (15)0.0170 (6)
H120.43820.47480.91600.020*
C130.39594 (15)0.4586 (2)0.82168 (15)0.0140 (5)
C140.33509 (14)0.3594 (2)0.71291 (14)0.0133 (5)
C150.35026 (15)0.3097 (2)0.77502 (14)0.0143 (5)
C160.33338 (15)0.2107 (2)0.78344 (15)0.0169 (6)
H160.34390.17600.82370.020*
C170.30006 (15)0.1646 (2)0.72952 (15)0.0163 (6)
H170.28800.09800.73520.020*
C180.28375 (15)0.2126 (2)0.66731 (15)0.0166 (6)
H180.26070.17940.63300.020*
C190.30282 (14)0.3101 (2)0.65858 (14)0.0142 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.00966 (11)0.00890 (12)0.00809 (11)0.00078 (8)0.00280 (8)0.00075 (8)
Mo20.00910 (11)0.00898 (12)0.00841 (11)0.00116 (8)0.00194 (9)0.00080 (8)
Mo30.01010 (11)0.00791 (11)0.00914 (11)0.00078 (8)0.00268 (9)0.00043 (8)
Cl10.0183 (3)0.0175 (3)0.0127 (3)0.0004 (3)0.0076 (3)0.0012 (2)
Cl20.0125 (3)0.0172 (3)0.0131 (3)0.0030 (3)0.0005 (2)0.0001 (2)
Cl30.0196 (3)0.0102 (3)0.0195 (3)0.0002 (3)0.0049 (3)0.0019 (3)
Cl40.0135 (3)0.0109 (3)0.0116 (3)0.0018 (2)0.0030 (2)0.0032 (2)
Cl50.0114 (3)0.0114 (3)0.0128 (3)0.0012 (2)0.0030 (2)0.0002 (2)
Cl60.0119 (3)0.0120 (3)0.0116 (3)0.0026 (2)0.0038 (2)0.0003 (2)
Cl70.0131 (3)0.0131 (3)0.0094 (3)0.0002 (2)0.0019 (2)0.0014 (2)
O10.0171 (10)0.0153 (10)0.0121 (9)0.0011 (8)0.0044 (8)0.0003 (7)
O20.0227 (10)0.0142 (10)0.0141 (9)0.0060 (8)0.0059 (8)0.0022 (8)
O30.0203 (10)0.0151 (10)0.0115 (9)0.0008 (8)0.0065 (8)0.0005 (7)
C10.0081 (12)0.0176 (14)0.0123 (13)0.0001 (10)0.0013 (10)0.0003 (10)
C20.0097 (12)0.0182 (14)0.0123 (13)0.0006 (11)0.0005 (10)0.0009 (11)
C30.0117 (13)0.0164 (14)0.0138 (13)0.0011 (11)0.0013 (11)0.0013 (10)
C40.0138 (13)0.0252 (15)0.0129 (14)0.0037 (12)0.0031 (11)0.0008 (11)
C50.0150 (13)0.0257 (15)0.0129 (13)0.0045 (12)0.0039 (11)0.0080 (12)
C60.0147 (13)0.0187 (15)0.0191 (14)0.0046 (11)0.0024 (11)0.0055 (11)
C70.0112 (13)0.0184 (14)0.0138 (13)0.0024 (11)0.0018 (10)0.0007 (11)
C80.0117 (13)0.0149 (14)0.0113 (13)0.0016 (10)0.0008 (10)0.0006 (10)
C90.0138 (13)0.0173 (14)0.0130 (13)0.0025 (11)0.0028 (11)0.0028 (11)
C100.0211 (15)0.0167 (14)0.0196 (15)0.0067 (12)0.0035 (12)0.0005 (12)
C110.0208 (15)0.0235 (16)0.0152 (14)0.0041 (12)0.0048 (12)0.0042 (12)
C120.0167 (14)0.0214 (15)0.0139 (13)0.0008 (12)0.0056 (11)0.0016 (11)
C130.0127 (13)0.0147 (14)0.0146 (13)0.0009 (11)0.0014 (11)0.0001 (10)
C140.0122 (13)0.0141 (13)0.0135 (13)0.0017 (10)0.0013 (10)0.0007 (10)
C150.0142 (13)0.0172 (14)0.0111 (12)0.0024 (11)0.0006 (10)0.0023 (11)
C160.0193 (14)0.0149 (14)0.0165 (14)0.0039 (11)0.0021 (11)0.0010 (11)
C170.0173 (14)0.0113 (13)0.0191 (14)0.0002 (11)0.0013 (11)0.0024 (11)
C180.0175 (14)0.0164 (14)0.0154 (13)0.0007 (11)0.0000 (11)0.0049 (11)
C190.0127 (13)0.0184 (14)0.0110 (12)0.0020 (11)0.0001 (10)0.0004 (11)
Geometric parameters (Å, º) top
Mo1—Cl12.4309 (9)O1—C31.374 (3)
Mo1—Cl72.4596 (8)O1—C191.380 (3)
Mo1—Cl42.4655 (7)O2—C91.378 (3)
Mo1—Cl5i2.4735 (8)O2—C71.379 (3)
Mo1—Cl62.4785 (7)O3—C151.383 (3)
Mo1—Mo2i2.6133 (7)O3—C131.376 (3)
Mo1—Mo3i2.6168 (5)C1—C21.391 (4)
Mo1—Mo22.6192 (6)C1—C81.396 (4)
Mo1—Mo32.6198 (5)C1—C141.394 (4)
Mo2—Cl22.4427 (10)C2—C31.406 (4)
Mo2—Cl42.4698 (8)C2—C71.410 (4)
Mo2—Cl72.4765 (8)C3—C41.381 (4)
Mo2—Cl6i2.4841 (8)C4—C51.398 (4)
Mo2—Cl52.4902 (8)C5—C61.393 (4)
Mo2—Mo32.6093 (5)C6—C71.382 (4)
Mo2—Mo1i2.6132 (7)C8—C91.406 (4)
Mo2—Mo3i2.6174 (7)C8—C131.412 (4)
Mo3—Cl32.4397 (8)C9—C101.382 (4)
Mo3—Cl52.4662 (8)C10—C111.394 (4)
Mo3—Cl62.4667 (8)C11—C121.400 (4)
Mo3—Cl72.4750 (8)C12—C131.384 (4)
Mo3—Cl4i2.4886 (8)C14—C151.401 (4)
Mo3—Mo1i2.6168 (5)C14—C191.409 (4)
Mo3—Mo2i2.6174 (7)C15—C161.379 (4)
Cl4—Mo3i2.4886 (8)C16—C171.393 (4)
Cl5—Mo1i2.4733 (9)C17—C181.399 (4)
Cl6—Mo2i2.4841 (7)C18—C191.369 (4)
Cl1—Mo1—Cl793.24 (3)Cl7—Mo3—Cl4i174.56 (2)
Cl1—Mo1—Cl492.23 (3)Cl3—Mo3—Mo2134.18 (2)
Cl7—Mo1—Cl489.41 (3)Cl5—Mo3—Mo258.682 (18)
Cl1—Mo1—Cl5i91.11 (3)Cl6—Mo3—Mo2118.335 (19)
Cl7—Mo1—Cl5i175.61 (2)Cl7—Mo3—Mo258.23 (2)
Cl4—Mo1—Cl5i89.86 (3)Cl4i—Mo3—Mo2117.66 (2)
Cl1—Mo1—Cl692.53 (3)Cl3—Mo3—Mo1i134.37 (2)
Cl7—Mo1—Cl689.42 (3)Cl5—Mo3—Mo1i58.14 (2)
Cl4—Mo1—Cl6175.15 (2)Cl6—Mo3—Mo1i118.45 (3)
Cl5i—Mo1—Cl690.95 (3)Cl7—Mo3—Mo1i118.20 (2)
Cl1—Mo1—Mo2i134.31 (2)Cl4i—Mo3—Mo1i57.687 (19)
Cl7—Mo1—Mo2i118.23 (3)Mo2—Mo3—Mo1i60.003 (16)
Cl4—Mo1—Mo2i118.37 (2)Cl3—Mo3—Mo2i135.90 (2)
Cl5i—Mo1—Mo2i58.54 (2)Cl5—Mo3—Mo2i118.19 (2)
Cl6—Mo1—Mo2i58.33 (2)Cl6—Mo3—Mo2i58.41 (2)
Cl1—Mo1—Mo3i134.27 (2)Cl7—Mo3—Mo2i117.50 (3)
Cl7—Mo1—Mo3i118.24 (2)Cl4i—Mo3—Mo2i57.79 (2)
Cl4—Mo1—Mo3i58.55 (2)Mo2—Mo3—Mo2i89.91 (2)
Cl5i—Mo1—Mo3i57.88 (2)Mo1i—Mo3—Mo2i60.054 (16)
Cl6—Mo1—Mo3i118.15 (2)Cl3—Mo3—Mo1135.49 (2)
Mo2i—Mo1—Mo3i59.855 (14)Cl5—Mo3—Mo1118.78 (2)
Cl1—Mo1—Mo2135.90 (3)Cl6—Mo3—Mo158.230 (19)
Cl7—Mo1—Mo258.27 (2)Cl7—Mo3—Mo157.65 (2)
Cl4—Mo1—Mo258.025 (18)Cl4i—Mo3—Mo1117.63 (2)
Cl5i—Mo1—Mo2117.85 (2)Mo2—Mo3—Mo160.118 (16)
Cl6—Mo1—Mo2117.52 (2)Mo1i—Mo3—Mo190.13 (2)
Mo2i—Mo1—Mo289.78 (3)Mo2i—Mo3—Mo159.865 (14)
Mo3i—Mo1—Mo259.98 (2)Mo1—Cl4—Mo264.11 (2)
Cl1—Mo1—Mo3135.85 (2)Mo1—Cl4—Mo3i63.77 (2)
Cl7—Mo1—Mo358.22 (2)Mo2—Cl4—Mo3i63.72 (2)
Cl4—Mo1—Mo3117.76 (2)Mo3—Cl5—Mo1i63.98 (2)
Cl5i—Mo1—Mo3118.54 (2)Mo3—Cl5—Mo263.53 (2)
Cl6—Mo1—Mo357.79 (2)Mo1i—Cl5—Mo263.54 (2)
Mo2i—Mo1—Mo360.022 (15)Mo3—Cl6—Mo163.979 (19)
Mo3i—Mo1—Mo389.87 (2)Mo3—Cl6—Mo2i63.83 (3)
Mo2—Mo1—Mo359.742 (14)Mo1—Cl6—Mo2i63.55 (2)
Cl2—Mo2—Cl492.01 (2)Mo1—Cl7—Mo364.13 (2)
Cl2—Mo2—Cl795.05 (3)Mo1—Cl7—Mo264.09 (2)
Cl4—Mo2—Cl788.92 (3)Mo3—Cl7—Mo263.60 (2)
Cl2—Mo2—Cl6i90.01 (3)C3—O1—C19120.6 (2)
Cl4—Mo2—Cl6i89.98 (3)C9—O2—C7120.5 (2)
Cl7—Mo2—Cl6i174.86 (2)C15—O3—C13120.2 (2)
Cl2—Mo2—Cl592.74 (2)C2—C1—C8119.8 (2)
Cl4—Mo2—Cl5175.23 (2)C2—C1—C14120.1 (2)
Cl7—Mo2—Cl590.25 (3)C8—C1—C14120.1 (2)
Cl6i—Mo2—Cl590.43 (3)C1—C2—C3119.6 (2)
Cl2—Mo2—Mo3136.77 (2)C1—C2—C7119.6 (2)
Cl4—Mo2—Mo3118.00 (2)C3—C2—C7120.8 (2)
Cl7—Mo2—Mo358.17 (2)O1—C3—C4120.1 (2)
Cl6i—Mo2—Mo3118.23 (2)O1—C3—C2120.2 (2)
Cl5—Mo2—Mo357.79 (2)C4—C3—C2119.7 (3)
Cl2—Mo2—Mo1i133.18 (3)C3—C4—C5118.1 (3)
Cl4—Mo2—Mo1i118.58 (2)C6—C5—C4123.6 (3)
Cl7—Mo2—Mo1i118.28 (2)C7—C6—C5117.8 (3)
Cl6i—Mo2—Mo1i58.122 (19)C6—C7—O2120.0 (2)
Cl5—Mo2—Mo1i57.919 (19)C6—C7—C2119.9 (3)
Mo3—Mo2—Mo1i60.140 (16)O2—C7—C2120.1 (2)
Cl2—Mo2—Mo3i133.09 (2)C1—C8—C9119.8 (2)
Cl4—Mo2—Mo3i58.490 (19)C1—C8—C13119.4 (2)
Cl7—Mo2—Mo3i117.59 (2)C9—C8—C13120.8 (2)
Cl6i—Mo2—Mo3i57.76 (2)C10—C9—O2119.9 (2)
Cl5—Mo2—Mo3i118.00 (2)C10—C9—C8120.1 (3)
Mo3—Mo2—Mo3i90.09 (2)O2—C9—C8120.0 (2)
Mo1i—Mo2—Mo3i60.11 (2)C9—C10—C11117.6 (3)
Cl2—Mo2—Mo1136.54 (2)C10—C11—C12124.2 (3)
Cl4—Mo2—Mo157.867 (19)C13—C12—C11117.5 (3)
Cl7—Mo2—Mo157.64 (2)O3—C13—C12119.9 (2)
Cl6i—Mo2—Mo1117.71 (3)O3—C13—C8120.2 (2)
Cl5—Mo2—Mo1117.91 (2)C12—C13—C8119.9 (2)
Mo3—Mo2—Mo160.140 (12)C15—C14—C1119.4 (2)
Mo1i—Mo2—Mo190.22 (3)C15—C14—C19121.2 (2)
Mo3i—Mo2—Mo159.962 (16)C1—C14—C19119.4 (2)
Cl3—Mo3—Cl590.94 (2)O3—C15—C16119.7 (2)
Cl3—Mo3—Cl692.97 (2)O3—C15—C14120.6 (2)
Cl5—Mo3—Cl6176.07 (2)C16—C15—C14119.7 (2)
Cl3—Mo3—Cl792.40 (2)C15—C16—C17117.8 (3)
Cl5—Mo3—Cl790.84 (4)C16—C17—C18123.7 (3)
Cl6—Mo3—Cl789.34 (3)C19—C18—C17117.9 (3)
Cl3—Mo3—Cl4i93.02 (2)C18—C19—O1120.3 (2)
Cl5—Mo3—Cl4i89.50 (4)C18—C19—C14119.7 (3)
Cl6—Mo3—Cl4i89.95 (4)O1—C19—C14120.0 (2)
Symmetry code: (i) x, y+1, z+1.
(10) Bis(4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium) dithionate top
Crystal data top
C19H9O3·O3SV = 689.8 (2) Å3
Mr = 365.32Z = 2
Triclinic, P1F(000) = 374
Hall symbol: -P 1Dx = 1.759 Mg m3
a = 8.6300 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9680 (18) ŵ = 0.28 mm1
c = 9.876 (2) ÅT = 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 tube2452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 2.2°
ω scan, frame data integrationh = 1010
Absorption correction: empirical (using intensity measurements)k = 1111
Tmin = 0.616, Tmax = 0.962l = 1212
5953 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1004P]
where P = (Fo2 + 2Fc2)/3
2779 reflections(Δ/σ)max = 0.002
235 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.50 e Å3
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
xyzUiso*/Ueq
S10.09095 (4)0.08812 (4)0.03601 (4)0.01374 (12)
O70.25338 (14)0.07534 (14)0.02557 (13)0.0254 (3)
O80.03366 (15)0.03780 (14)0.18974 (12)0.0286 (3)
O90.08044 (15)0.24187 (13)0.01992 (13)0.0255 (3)
O10.37974 (13)0.38610 (12)0.14184 (11)0.0171 (2)
O20.49125 (14)0.83946 (12)0.36618 (11)0.0189 (2)
O30.82405 (13)0.49878 (13)0.37918 (12)0.0189 (2)
C10.56952 (18)0.57924 (17)0.28984 (15)0.0147 (3)
C20.43809 (19)0.61505 (17)0.25103 (15)0.0153 (3)
C30.34140 (19)0.51602 (17)0.17734 (15)0.0163 (3)
C40.20936 (19)0.54894 (19)0.13989 (16)0.0197 (3)
H40.14290.48330.09290.024*
C50.17824 (19)0.6845 (2)0.17483 (17)0.0215 (3)
H50.09110.70920.14750.026*
C60.2710 (2)0.78490 (18)0.24865 (17)0.0208 (3)
H60.24620.87390.27030.025*
C70.39998 (19)0.74797 (17)0.28820 (16)0.0171 (3)
C80.66195 (19)0.67269 (17)0.36837 (15)0.0160 (3)
C90.61880 (19)0.80211 (17)0.40795 (16)0.0172 (3)
C100.7001 (2)0.88712 (18)0.49493 (17)0.0215 (3)
H100.67370.97340.52190.026*
C110.8226 (2)0.84029 (18)0.54116 (16)0.0219 (3)
H110.87610.89640.60090.026*
C120.8691 (2)0.71312 (19)0.50226 (16)0.0208 (3)
H120.95240.68570.53420.025*
C130.78726 (19)0.62956 (17)0.41471 (16)0.0171 (3)
C140.60521 (18)0.44509 (17)0.25648 (15)0.0151 (3)
C150.73563 (19)0.40754 (17)0.29924 (16)0.0167 (3)
C160.7746 (2)0.27802 (18)0.26240 (17)0.0199 (3)
H160.86250.25270.28770.024*
C170.6775 (2)0.18627 (17)0.18595 (16)0.0199 (3)
H170.70420.09970.16000.024*
C180.5433 (2)0.21684 (17)0.14640 (16)0.0184 (3)
H180.47940.15080.09810.022*
C190.50842 (18)0.34897 (17)0.18146 (15)0.0157 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01485 (19)0.01360 (19)0.0152 (2)0.00554 (14)0.00625 (14)0.00659 (13)
O70.0167 (6)0.0273 (6)0.0388 (7)0.0097 (5)0.0102 (5)0.0201 (5)
O80.0323 (7)0.0318 (7)0.0149 (6)0.0009 (5)0.0079 (5)0.0077 (5)
O90.0295 (6)0.0151 (6)0.0396 (7)0.0090 (5)0.0209 (6)0.0106 (5)
O10.0186 (5)0.0153 (5)0.0170 (5)0.0045 (4)0.0057 (4)0.0053 (4)
O20.0231 (6)0.0148 (5)0.0191 (6)0.0072 (4)0.0042 (5)0.0063 (4)
O30.0189 (5)0.0191 (5)0.0199 (5)0.0072 (4)0.0069 (4)0.0052 (4)
C10.0152 (7)0.0119 (7)0.0106 (7)0.0008 (6)0.0015 (6)0.0001 (6)
C20.0158 (7)0.0130 (7)0.0124 (7)0.0026 (6)0.0000 (6)0.0001 (6)
C30.0185 (7)0.0136 (7)0.0122 (7)0.0033 (6)0.0006 (6)0.0002 (6)
C40.0178 (7)0.0223 (8)0.0143 (7)0.0035 (6)0.0033 (6)0.0001 (6)
C50.0177 (8)0.0254 (8)0.0168 (8)0.0083 (6)0.0000 (6)0.0040 (6)
C60.0218 (8)0.0177 (7)0.0195 (8)0.0091 (6)0.0008 (6)0.0011 (6)
C70.0193 (7)0.0142 (7)0.0133 (7)0.0036 (6)0.0006 (6)0.0011 (6)
C80.0172 (7)0.0136 (7)0.0116 (7)0.0013 (6)0.0003 (6)0.0014 (6)
C90.0184 (7)0.0139 (7)0.0137 (7)0.0020 (6)0.0002 (6)0.0013 (6)
C100.0257 (8)0.0149 (7)0.0156 (7)0.0000 (6)0.0010 (6)0.0049 (6)
C110.0218 (8)0.0195 (8)0.0145 (7)0.0037 (6)0.0020 (6)0.0045 (6)
C120.0175 (7)0.0232 (8)0.0146 (7)0.0005 (6)0.0030 (6)0.0002 (6)
C130.0165 (7)0.0149 (7)0.0149 (7)0.0024 (6)0.0001 (6)0.0021 (6)
C140.0157 (7)0.0130 (7)0.0125 (7)0.0031 (6)0.0005 (6)0.0012 (6)
C150.0163 (7)0.0150 (7)0.0144 (7)0.0027 (6)0.0011 (6)0.0017 (6)
C160.0193 (8)0.0179 (7)0.0198 (8)0.0085 (6)0.0003 (6)0.0005 (6)
C170.0243 (8)0.0123 (7)0.0172 (7)0.0062 (6)0.0037 (6)0.0006 (6)
C180.0224 (8)0.0132 (7)0.0134 (7)0.0019 (6)0.0005 (6)0.0028 (6)
C190.0161 (7)0.0143 (7)0.0121 (7)0.0028 (6)0.0001 (6)0.0008 (6)
Geometric parameters (Å, º) top
S1—O81.4493 (12)C4—C51.397 (2)
S1—O71.4507 (12)C5—C61.398 (2)
S1—O91.4512 (12)C6—C71.374 (2)
S1—S1i2.1616 (10)C8—C131.400 (2)
O1—C191.3724 (18)C8—C91.406 (2)
O1—C31.3779 (18)C9—C101.381 (2)
O2—C91.3733 (19)C10—C111.393 (2)
O2—C71.3813 (18)C11—C121.399 (2)
O3—C131.3793 (18)C12—C131.382 (2)
O3—C151.3829 (18)C14—C151.402 (2)
C1—C21.386 (2)C14—C191.404 (2)
C1—C141.397 (2)C15—C161.381 (2)
C1—C81.399 (2)C16—C171.397 (2)
C2—C31.407 (2)C17—C181.391 (2)
C2—C71.408 (2)C18—C191.382 (2)
C3—C41.374 (2)
O8—S1—O7113.75 (8)C1—C8—C13119.76 (13)
O8—S1—O9114.14 (8)C1—C8—C9119.11 (14)
O7—S1—O9113.22 (8)C13—C8—C9120.98 (14)
O8—S1—S1i104.55 (6)O2—C9—C10119.94 (13)
O7—S1—S1i104.83 (5)O2—C9—C8120.42 (13)
O9—S1—S1i105.05 (5)C10—C9—C8119.57 (14)
C19—O1—C3120.65 (12)C9—C10—C11118.29 (14)
C9—O2—C7120.69 (11)C10—C11—C12123.30 (14)
C13—O3—C15120.29 (12)C13—C12—C11117.78 (14)
C2—C1—C14120.15 (13)O3—C13—C12119.52 (14)
C2—C1—C8120.18 (13)O3—C13—C8120.34 (13)
C14—C1—C8119.60 (14)C12—C13—C8120.07 (14)
C1—C2—C3119.63 (13)C1—C14—C15119.74 (13)
C1—C2—C7119.85 (14)C1—C14—C19119.28 (14)
C3—C2—C7120.50 (14)C15—C14—C19120.97 (13)
C4—C3—O1119.84 (13)C16—C15—O3120.03 (14)
C4—C3—C2120.21 (14)C16—C15—C14119.77 (14)
O1—C3—C2119.95 (13)O3—C15—C14120.20 (13)
C3—C4—C5117.75 (14)C15—C16—C17117.79 (14)
C4—C5—C6123.56 (14)C18—C17—C16123.82 (13)
C7—C6—C5117.89 (14)C19—C18—C17117.62 (14)
C6—C7—O2120.26 (13)O1—C19—C18119.72 (13)
C6—C7—C2120.04 (14)O1—C19—C14120.31 (13)
O2—C7—C2119.70 (13)C18—C19—C14119.96 (14)
Symmetry code: (i) x, y, z.
(11) 2,6,10-tri-tert-butyl-4,8,12-trioxa-4,8,12,12c-tetrahydro- dibenzo[cd,mn]pyrenium hexafluorophosphate acetonitrile top
Crystal data top
C31H33O3·F6P·C2H3NZ = 4
Mr = 639.60F(000) = 1336
Monoclinic, P21/nDx = 1.386 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.085 (2) ŵ = 0.16 mm1
b = 11.347 (2) ÅT = 120 K
c = 22.930 (5) ÅPlate, 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 tube5092 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 1.8°
ω scan, frame data integrationh = 1515
Absorption correction: empirical (using intensity measurements)k = 1414
Tmin = 0.853, Tmax = 0.978l = 2828
31555 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.04Calculated w = 1/[σ2(Fo2) + (0.0441P)2 + 1.7107P]
where P = (Fo2 + 2Fc2)/3
6252 reflections(Δ/σ)max = 0.054
434 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.39 e Å3
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
xyzUiso*/UeqOcc. (<1)
P10.34656 (3)0.41333 (4)0.101226 (17)0.02354 (11)
F10.29677 (10)0.32970 (9)0.04514 (4)0.0405 (3)
F20.46557 (9)0.34492 (9)0.11102 (5)0.0449 (3)
F30.22908 (9)0.48232 (10)0.09040 (6)0.0463 (3)
F40.38972 (9)0.50418 (9)0.05780 (5)0.0417 (3)
F50.39743 (11)0.49646 (11)0.15628 (5)0.0546 (3)
F60.30390 (12)0.32194 (11)0.14362 (5)0.0555 (3)
O10.46862 (8)0.22621 (9)0.08095 (4)0.0194 (2)
O20.75326 (8)0.06305 (9)0.01318 (4)0.0200 (2)
O30.37139 (8)0.12015 (9)0.12786 (4)0.0188 (2)
C10.53172 (12)0.13935 (12)0.02060 (6)0.0166 (3)
C20.61116 (12)0.14647 (12)0.03352 (6)0.0171 (3)
C30.57861 (12)0.18952 (12)0.08450 (6)0.0181 (3)
C40.65619 (13)0.19360 (13)0.13862 (6)0.0210 (3)
H40.63520.22310.17240.025*
C50.76712 (13)0.15266 (13)0.14209 (7)0.0221 (3)
C60.80038 (12)0.11075 (13)0.09060 (7)0.0215 (3)
H60.87450.08550.09300.026*
C70.72266 (12)0.10755 (13)0.03697 (6)0.0188 (3)
C80.56226 (12)0.09261 (12)0.07064 (6)0.0167 (3)
C90.67409 (12)0.05414 (13)0.06657 (6)0.0181 (3)
C100.70406 (12)0.00474 (13)0.11556 (7)0.0209 (3)
H100.77800.02090.11310.025*
C110.62246 (13)0.00680 (13)0.16937 (7)0.0212 (3)
C120.51048 (12)0.03404 (13)0.17420 (6)0.0199 (3)
H120.45720.02800.21020.024*
C130.48143 (12)0.08286 (12)0.12474 (6)0.0172 (3)
C140.42035 (12)0.17520 (12)0.02379 (6)0.0165 (3)
C150.34000 (12)0.16487 (12)0.07793 (6)0.0172 (3)
C160.22893 (12)0.19625 (13)0.08075 (6)0.0196 (3)
H160.17550.19130.11680.023*
C170.19662 (12)0.23599 (12)0.02861 (7)0.0196 (3)
C180.27771 (12)0.24856 (13)0.02539 (6)0.0194 (3)
H180.25660.27730.05930.023*
C190.38880 (12)0.21785 (12)0.02762 (6)0.0174 (3)
C200.85462 (14)0.14830 (15)0.20174 (7)0.0278 (4)
C210.81103 (15)0.20551 (16)0.25274 (7)0.0328 (4)
H21A0.86850.20060.28910.049*
H21B0.74400.16510.25780.049*
H21C0.79330.28670.24330.049*
C220.96215 (16)0.2141 (2)0.19535 (9)0.0433 (5)
H22A1.01750.21090.23250.065*
H22B0.94370.29490.18500.065*
H22C0.99260.17790.16450.065*
C230.88260 (16)0.01823 (17)0.21726 (7)0.0364 (4)
H23A0.93770.01340.25450.055*
H23B0.91280.01750.18610.055*
H23C0.81480.02250.22080.055*
C240.65476 (16)0.06527 (16)0.22341 (7)0.0331 (4)
C250.7698 (3)0.1145 (3)0.21274 (12)0.0346 (8)0.647 (4)
H25A0.78200.14910.24900.052*0.65
H25B0.77850.17370.18220.052*0.65
H25C0.82430.05280.20010.052*0.65
C260.5685 (3)0.1779 (3)0.24179 (13)0.0363 (8)0.647 (4)
H26A0.49130.15100.24930.055*0.65
H26B0.58140.23400.20960.055*0.65
H26C0.58240.21460.27720.055*0.65
C270.6281 (3)0.0164 (3)0.27750 (12)0.0340 (8)0.647 (4)
H27A0.55200.04570.28260.051*0.65
H27B0.63500.02640.31260.051*0.65
H27C0.68040.08120.27140.051*0.65
C25U0.7159 (5)0.1793 (5)0.2033 (2)0.0319 (13)0.353 (4)
H25D0.785 (5)0.182 (5)0.168 (3)0.048*0.353 (4)
H25E0.745 (5)0.211 (5)0.242 (3)0.048*0.353 (4)
H25F0.652 (5)0.242 (5)0.194 (3)0.048*0.353 (4)
C26U0.5761 (5)0.0654 (6)0.2765 (2)0.0385 (16)0.353 (4)
H26D0.54310.01170.28380.058*0.35
H26E0.51770.12170.27470.058*0.35
H26F0.61220.08620.30840.058*0.35
C27U0.7648 (5)0.0248 (5)0.2334 (2)0.0380 (14)0.353 (4)
H27D0.82230.02740.19700.057*0.35
H27E0.73630.10290.24350.057*0.35
H27F0.79650.00600.26500.057*0.35
C280.07196 (13)0.26874 (14)0.03214 (7)0.0237 (3)
C290.04331 (15)0.2709 (2)0.02972 (8)0.0416 (5)
H29A0.09300.32500.05520.062*
H29B0.05300.19340.04690.062*
H29C0.03400.29560.02580.062*
C300.05239 (16)0.39257 (18)0.05877 (10)0.0436 (5)
H30A0.10330.44690.03420.065*
H30B0.02460.41600.06040.065*
H30C0.06620.39250.09840.065*
C310.00802 (15)0.1819 (2)0.07142 (11)0.0510 (6)
H31A0.08520.20510.07350.077*
H31B0.00430.10430.05450.077*
H31C0.00650.18170.11090.077*
N10.80951 (15)0.51476 (16)0.18129 (7)0.0441 (4)
C320.74631 (15)0.51537 (15)0.13629 (8)0.0305 (4)
C330.66667 (17)0.51612 (17)0.07866 (8)0.0382 (4)
H33A0.66540.43980.06050.057*
H33B0.68970.57410.05330.057*
H33C0.59220.53500.08410.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0252 (2)0.0245 (2)0.0202 (2)0.00229 (16)0.00342 (16)0.00158 (15)
F10.0531 (7)0.0334 (6)0.0302 (5)0.0000 (5)0.0011 (5)0.0093 (4)
F20.0330 (6)0.0319 (6)0.0653 (8)0.0104 (5)0.0012 (5)0.0002 (5)
F30.0264 (6)0.0448 (6)0.0673 (8)0.0082 (5)0.0093 (5)0.0077 (6)
F40.0453 (6)0.0344 (6)0.0477 (6)0.0000 (5)0.0154 (5)0.0111 (5)
F50.0692 (9)0.0462 (7)0.0367 (6)0.0069 (6)0.0134 (6)0.0190 (5)
F60.0782 (9)0.0528 (7)0.0427 (7)0.0055 (6)0.0292 (6)0.0126 (6)
O10.0192 (5)0.0231 (5)0.0156 (5)0.0019 (4)0.0029 (4)0.0019 (4)
O20.0159 (5)0.0265 (5)0.0172 (5)0.0019 (4)0.0027 (4)0.0002 (4)
O30.0165 (5)0.0248 (5)0.0149 (5)0.0034 (4)0.0030 (4)0.0006 (4)
C10.0187 (7)0.0129 (6)0.0185 (7)0.0022 (5)0.0045 (6)0.0020 (5)
C20.0175 (7)0.0161 (7)0.0172 (7)0.0015 (5)0.0028 (5)0.0015 (5)
C30.0185 (7)0.0161 (7)0.0196 (7)0.0016 (5)0.0043 (6)0.0005 (5)
C40.0236 (8)0.0214 (7)0.0180 (7)0.0024 (6)0.0044 (6)0.0019 (6)
C50.0224 (8)0.0219 (7)0.0199 (7)0.0050 (6)0.0005 (6)0.0003 (6)
C60.0163 (7)0.0242 (7)0.0228 (8)0.0004 (6)0.0017 (6)0.0019 (6)
C70.0192 (7)0.0185 (7)0.0193 (7)0.0023 (5)0.0053 (6)0.0004 (5)
C80.0179 (7)0.0163 (7)0.0165 (7)0.0004 (5)0.0049 (5)0.0021 (5)
C90.0182 (7)0.0189 (7)0.0172 (7)0.0004 (5)0.0035 (6)0.0033 (5)
C100.0190 (7)0.0236 (7)0.0215 (7)0.0048 (6)0.0077 (6)0.0036 (6)
C110.0250 (8)0.0221 (7)0.0180 (7)0.0041 (6)0.0077 (6)0.0030 (6)
C120.0215 (7)0.0230 (7)0.0149 (7)0.0024 (6)0.0031 (6)0.0009 (6)
C130.0168 (7)0.0167 (7)0.0187 (7)0.0007 (5)0.0049 (5)0.0022 (5)
C140.0178 (7)0.0147 (6)0.0175 (7)0.0004 (5)0.0050 (5)0.0013 (5)
C150.0205 (7)0.0168 (7)0.0154 (7)0.0001 (5)0.0061 (6)0.0008 (5)
C160.0178 (7)0.0212 (7)0.0188 (7)0.0006 (6)0.0022 (6)0.0012 (6)
C170.0193 (7)0.0159 (7)0.0242 (7)0.0013 (5)0.0064 (6)0.0026 (6)
C180.0220 (8)0.0179 (7)0.0198 (7)0.0014 (6)0.0081 (6)0.0004 (6)
C190.0207 (7)0.0153 (7)0.0160 (7)0.0007 (5)0.0036 (6)0.0007 (5)
C200.0238 (8)0.0357 (9)0.0200 (8)0.0020 (7)0.0035 (6)0.0038 (7)
C210.0354 (10)0.0380 (9)0.0200 (8)0.0002 (8)0.0046 (7)0.0051 (7)
C220.0257 (9)0.0637 (13)0.0356 (10)0.0118 (9)0.0038 (8)0.0088 (9)
C230.0379 (10)0.0423 (10)0.0223 (8)0.0100 (8)0.0076 (7)0.0016 (7)
C240.0416 (10)0.0391 (10)0.0210 (8)0.0191 (8)0.0124 (7)0.0008 (7)
C250.0299 (15)0.0520 (19)0.0226 (13)0.0166 (15)0.0070 (11)0.0056 (12)
C260.0408 (17)0.0370 (16)0.0327 (15)0.0028 (12)0.0112 (12)0.0135 (12)
C270.0383 (16)0.0459 (19)0.0214 (13)0.0132 (14)0.0142 (11)0.0047 (12)
C25U0.035 (3)0.031 (3)0.031 (3)0.009 (2)0.008 (2)0.004 (2)
C26U0.040 (3)0.055 (4)0.021 (2)0.019 (3)0.007 (2)0.009 (2)
C27U0.051 (3)0.043 (3)0.028 (3)0.008 (2)0.024 (2)0.004 (2)
C280.0174 (7)0.0285 (8)0.0258 (8)0.0037 (6)0.0062 (6)0.0010 (6)
C290.0240 (9)0.0685 (14)0.0360 (10)0.0106 (9)0.0144 (8)0.0092 (9)
C300.0297 (10)0.0419 (11)0.0628 (13)0.0171 (8)0.0183 (9)0.0190 (10)
C310.0189 (9)0.0645 (14)0.0711 (15)0.0061 (9)0.0128 (9)0.0321 (12)
N10.0475 (10)0.0495 (10)0.0333 (9)0.0025 (8)0.0049 (8)0.0001 (7)
C320.0332 (9)0.0293 (9)0.0318 (9)0.0012 (7)0.0134 (8)0.0011 (7)
C330.0407 (11)0.0340 (10)0.0366 (10)0.0029 (8)0.0015 (8)0.0000 (8)
Geometric parameters (Å, º) top
P1—F61.5842 (12)C10—C111.404 (2)
P1—F51.5861 (11)C11—C121.411 (2)
P1—F31.5916 (11)C11—C241.531 (2)
P1—F41.5993 (11)C12—C131.376 (2)
P1—F11.6037 (11)C14—C151.400 (2)
P1—F21.6055 (11)C14—C191.403 (2)
O1—C31.3780 (18)C15—C161.376 (2)
O1—C191.3818 (17)C16—C171.412 (2)
O2—C91.3794 (17)C17—C181.405 (2)
O2—C71.3797 (17)C17—C281.536 (2)
O3—C151.3806 (17)C18—C191.377 (2)
O3—C131.3821 (17)C20—C211.530 (2)
C1—C81.387 (2)C20—C221.534 (2)
C1—C21.392 (2)C20—C231.538 (3)
C1—C141.392 (2)C24—C26U1.368 (5)
C2—C31.402 (2)C24—C251.468 (3)
C2—C71.403 (2)C24—C25U1.510 (5)
C3—C41.380 (2)C24—C271.524 (3)
C4—C51.404 (2)C24—C261.644 (3)
C5—C61.412 (2)C24—C27U1.732 (6)
C5—C201.532 (2)C28—C311.526 (2)
C6—C71.372 (2)C28—C301.529 (2)
C8—C131.402 (2)C28—C291.534 (2)
C8—C91.403 (2)N1—C321.139 (2)
C9—C101.374 (2)C32—C331.451 (3)
F6—P1—F591.27 (7)C1—C14—C15119.57 (13)
F6—P1—F390.96 (7)C1—C14—C19119.80 (13)
F5—P1—F390.33 (7)C15—C14—C19120.60 (13)
F6—P1—F4179.22 (7)C16—C15—O3120.09 (13)
F5—P1—F489.42 (7)C16—C15—C14119.77 (13)
F3—P1—F489.38 (7)O3—C15—C14120.11 (12)
F6—P1—F189.40 (7)C15—C16—C17119.57 (13)
F5—P1—F1179.13 (7)C18—C17—C16120.58 (13)
F3—P1—F190.21 (7)C18—C17—C28120.35 (13)
F4—P1—F189.90 (6)C16—C17—C28119.05 (13)
F6—P1—F290.09 (7)C19—C18—C17119.33 (13)
F5—P1—F290.00 (7)C18—C19—O1119.87 (12)
F3—P1—F2178.90 (7)C18—C19—C14120.09 (13)
F4—P1—F289.57 (6)O1—C19—C14120.02 (13)
F1—P1—F289.45 (7)C21—C20—C5112.46 (14)
C3—O1—C19120.37 (11)C21—C20—C22108.04 (14)
C9—O2—C7120.32 (11)C5—C20—C22109.26 (14)
C15—O3—C13120.56 (11)C21—C20—C23109.01 (14)
C8—C1—C2120.13 (13)C5—C20—C23108.06 (13)
C8—C1—C14120.04 (13)C22—C20—C23110.00 (15)
C2—C1—C14119.78 (13)C26U—C24—C25126.4 (3)
C1—C2—C3119.85 (13)C26U—C24—C25U117.8 (3)
C1—C2—C7119.67 (13)C25—C24—C25U40.7 (2)
C3—C2—C7120.46 (13)C26U—C24—C2745.3 (3)
O1—C3—C4119.75 (13)C25—C24—C27112.8 (2)
O1—C3—C2120.15 (13)C25U—C24—C27140.3 (3)
C4—C3—C2120.09 (13)C26U—C24—C11118.0 (2)
C3—C4—C5119.26 (14)C25—C24—C11115.65 (16)
C4—C5—C6120.68 (13)C25U—C24—C11108.7 (2)
C4—C5—C20121.44 (14)C27—C24—C11110.45 (16)
C6—C5—C20117.86 (14)C26U—C24—C2659.7 (3)
C7—C6—C5119.54 (14)C25—C24—C26105.7 (2)
C6—C7—O2119.99 (13)C25U—C24—C2669.6 (3)
C6—C7—C2119.96 (13)C27—C24—C26104.9 (2)
O2—C7—C2120.02 (13)C11—C24—C26106.45 (15)
C1—C8—C13120.06 (13)C26U—C24—C27U106.6 (3)
C1—C8—C9119.59 (13)C25—C24—C27U61.3 (3)
C13—C8—C9120.35 (13)C25U—C24—C27U102.0 (3)
C10—C9—O2119.89 (13)C27—C24—C27U64.1 (2)
C10—C9—C8119.85 (13)C11—C24—C27U101.1 (2)
O2—C9—C8120.24 (12)C26—C24—C27U152.5 (2)
C9—C10—C11119.68 (13)C31—C28—C30109.66 (16)
C10—C11—C12120.80 (13)C31—C28—C29108.20 (15)
C10—C11—C24119.75 (14)C30—C28—C29107.94 (15)
C12—C11—C24119.45 (14)C31—C28—C17111.09 (13)
C13—C12—C11118.92 (13)C30—C28—C17107.81 (13)
C12—C13—O3119.98 (13)C29—C28—C17112.08 (13)
C12—C13—C8120.37 (13)N1—C32—C33179.44 (19)
O3—C13—C8119.64 (12)
(12) Bis(2,6,10-tri-tert-butyl-4,8,12-trioxa-4,8,12,12c-tetrahydro- dibenzo[cd,mn]pyrenium) tetradecachlorohexamolybdate top
Crystal data top
C31H33O3·Cl7Mo3Z = 4
Mr = 989.54F(000) = 1952
Monoclinic, P21/nDx = 1.877 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 17.157 (3) ŵ = 1.62 mm1
b = 11.130 (2) ÅT = 120 K
c = 18.456 (4) ÅCube, 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 tube6258 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scan, frame data integrationθmax = 26.4°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements)h = 2121
Tmin = 0.704, Tmax = 0.886k = 1313
36072 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 1.10Calculated w = 1/[σ2(Fo2) + (0.0303P)2 + 1.6569P]
where P = (Fo2 + 2Fc2)/3
7149 reflections(Δ/σ)max = 0.005
397 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 1.31 e Å3
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
xyzUiso*/Ueq
Mo10.950784 (10)0.876155 (17)0.043899 (10)0.01156 (5)
Mo21.014830 (10)1.079316 (17)0.088032 (10)0.01214 (5)
Mo31.095215 (10)0.923207 (17)0.021136 (10)0.01187 (5)
Cl10.88433 (3)0.71653 (5)0.10371 (3)0.02044 (12)
Cl21.03377 (4)1.17836 (6)0.20545 (3)0.02654 (14)
Cl31.22017 (3)0.81908 (5)0.04631 (3)0.02215 (13)
Cl40.87735 (3)1.03036 (5)0.10448 (3)0.01702 (12)
Cl51.15006 (3)1.12096 (5)0.06237 (3)0.01617 (11)
Cl61.02882 (3)0.73467 (5)0.02202 (3)0.01627 (11)
Cl71.05821 (3)0.88635 (5)0.14517 (3)0.01713 (11)
O10.45707 (8)0.82772 (14)0.15806 (8)0.0135 (3)
O20.31766 (8)1.08819 (14)0.00779 (8)0.0139 (3)
O30.49862 (8)0.79292 (14)0.10404 (8)0.0143 (3)
C10.42274 (12)0.90108 (19)0.02062 (12)0.0116 (4)
C20.38625 (12)0.9570 (2)0.08306 (12)0.0126 (4)
C30.40530 (12)0.92167 (19)0.15203 (12)0.0130 (4)
C40.37376 (12)0.9821 (2)0.21344 (11)0.0140 (4)
H40.38630.95950.25920.017*
C50.32230 (12)1.0787 (2)0.20608 (12)0.0136 (4)
C60.30081 (12)1.1120 (2)0.13717 (12)0.0147 (4)
H60.26481.17340.13310.018*
C70.33425 (12)1.0517 (2)0.07596 (12)0.0132 (4)
C80.40717 (12)0.93901 (19)0.04778 (12)0.0121 (4)
C90.35416 (12)1.0337 (2)0.05407 (12)0.0130 (4)
C100.33960 (12)1.07279 (19)0.12195 (12)0.0137 (4)
H100.30591.13710.12640.016*
C110.37588 (12)1.01525 (19)0.18422 (12)0.0128 (4)
C120.42924 (12)0.9201 (2)0.17862 (12)0.0137 (4)
H120.45340.88270.22030.016*
C130.44492 (12)0.88392 (19)0.11086 (12)0.0124 (4)
C140.47708 (12)0.80968 (19)0.02700 (11)0.0125 (4)
C150.51501 (12)0.75612 (19)0.03610 (11)0.0123 (4)
C160.56837 (12)0.6654 (2)0.02997 (12)0.0138 (4)
H160.59410.63000.07160.017*
C170.58391 (12)0.62647 (19)0.03938 (12)0.0134 (4)
C180.54567 (12)0.6798 (2)0.10273 (12)0.0137 (4)
H180.55570.65310.14850.016*
C190.49324 (12)0.7719 (2)0.09639 (11)0.0127 (4)
C200.28787 (13)1.1522 (2)0.27219 (12)0.0168 (5)
C210.19862 (14)1.1307 (2)0.28355 (13)0.0215 (5)
H21A0.17631.15090.23970.032*
H21B0.18851.04760.29510.032*
H21C0.17561.18000.32290.032*
C220.32445 (14)1.1189 (2)0.34166 (13)0.0232 (5)
H22A0.38001.13230.33410.035*
H22B0.30181.16770.38140.035*
H22C0.31441.03570.35290.035*
C230.30369 (15)1.2866 (2)0.25642 (13)0.0236 (5)
H23A0.35921.30050.24910.035*
H23B0.28071.30950.21340.035*
H23C0.28101.33360.29700.035*
C240.35515 (13)1.0489 (2)0.26010 (12)0.0171 (5)
C250.30681 (14)1.1646 (2)0.25967 (13)0.0229 (5)
H25A0.26021.15620.22610.034*
H25B0.33741.23070.24500.034*
H25C0.29251.17940.30770.034*
C260.43001 (16)1.0650 (3)0.31308 (14)0.0298 (6)
H26A0.41611.08550.36050.045*
H26B0.46131.12810.29580.045*
H26C0.45940.99140.31600.045*
C270.30638 (18)0.9441 (3)0.28503 (16)0.0346 (7)
H27A0.26000.93420.25140.052*
H27B0.29180.96090.33270.052*
H27C0.33690.87160.28660.052*
C280.64667 (12)0.5300 (2)0.04476 (12)0.0143 (4)
C290.63263 (14)0.4595 (2)0.11678 (13)0.0203 (5)
H29A0.63280.51400.15710.031*
H29B0.58280.41950.11950.031*
H29C0.67350.40100.11870.031*
C300.72640 (14)0.5947 (2)0.03938 (14)0.0228 (5)
H30A0.73440.63840.00570.034*
H30B0.72700.64950.07950.034*
H30C0.76750.53660.04100.034*
C310.64836 (14)0.4411 (2)0.01860 (14)0.0219 (5)
H31A0.65520.48410.06390.033*
H31B0.69110.38600.01660.033*
H31C0.59990.39730.01500.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.01039 (9)0.01106 (10)0.01335 (10)0.00042 (7)0.00189 (7)0.00083 (7)
Mo20.01238 (9)0.01202 (10)0.01198 (10)0.00028 (7)0.00120 (7)0.00290 (7)
Mo30.00936 (9)0.01110 (10)0.01507 (10)0.00076 (7)0.00105 (7)0.00121 (7)
Cl10.0187 (3)0.0178 (3)0.0252 (3)0.0031 (2)0.0044 (2)0.0046 (2)
Cl20.0354 (3)0.0265 (3)0.0173 (3)0.0032 (3)0.0011 (2)0.0103 (2)
Cl30.0127 (2)0.0180 (3)0.0352 (3)0.0039 (2)0.0003 (2)0.0011 (2)
Cl40.0158 (3)0.0175 (3)0.0190 (3)0.0003 (2)0.0074 (2)0.0028 (2)
Cl50.0120 (2)0.0156 (3)0.0203 (3)0.00195 (19)0.0012 (2)0.0021 (2)
Cl60.0158 (2)0.0117 (3)0.0215 (3)0.0010 (2)0.0030 (2)0.0031 (2)
Cl70.0182 (3)0.0174 (3)0.0150 (3)0.0000 (2)0.0013 (2)0.0017 (2)
O10.0156 (7)0.0132 (8)0.0118 (7)0.0033 (6)0.0023 (6)0.0004 (6)
O20.0133 (7)0.0150 (8)0.0137 (8)0.0036 (6)0.0032 (6)0.0012 (6)
O30.0161 (7)0.0145 (8)0.0126 (7)0.0042 (6)0.0032 (6)0.0008 (6)
C10.0097 (9)0.0091 (10)0.0162 (11)0.0030 (8)0.0027 (8)0.0001 (8)
C20.0105 (10)0.0121 (11)0.0154 (11)0.0002 (8)0.0021 (8)0.0020 (8)
C30.0103 (10)0.0118 (11)0.0169 (11)0.0009 (8)0.0022 (8)0.0000 (9)
C40.0139 (10)0.0162 (12)0.0121 (10)0.0013 (9)0.0028 (8)0.0003 (9)
C50.0114 (10)0.0131 (11)0.0161 (11)0.0019 (8)0.0012 (8)0.0023 (9)
C60.0125 (10)0.0127 (11)0.0190 (11)0.0019 (8)0.0028 (9)0.0015 (9)
C70.0110 (10)0.0143 (11)0.0144 (11)0.0019 (8)0.0027 (8)0.0011 (9)
C80.0112 (10)0.0113 (11)0.0143 (11)0.0015 (8)0.0033 (8)0.0002 (8)
C90.0113 (10)0.0130 (11)0.0146 (11)0.0015 (8)0.0016 (8)0.0016 (9)
C100.0103 (10)0.0127 (11)0.0184 (11)0.0018 (8)0.0035 (8)0.0027 (9)
C110.0115 (10)0.0123 (11)0.0154 (11)0.0053 (8)0.0048 (8)0.0032 (9)
C120.0147 (10)0.0134 (11)0.0130 (11)0.0020 (8)0.0013 (8)0.0022 (9)
C130.0115 (10)0.0091 (11)0.0171 (11)0.0007 (8)0.0034 (8)0.0016 (8)
C140.0119 (10)0.0103 (10)0.0159 (11)0.0012 (8)0.0039 (8)0.0013 (8)
C150.0121 (10)0.0118 (11)0.0136 (10)0.0010 (8)0.0040 (8)0.0012 (8)
C160.0146 (10)0.0127 (11)0.0139 (10)0.0010 (8)0.0004 (8)0.0020 (9)
C170.0114 (10)0.0105 (11)0.0189 (11)0.0021 (8)0.0042 (8)0.0003 (9)
C180.0141 (10)0.0135 (11)0.0142 (10)0.0017 (8)0.0043 (8)0.0013 (9)
C190.0112 (10)0.0123 (11)0.0149 (11)0.0013 (8)0.0034 (8)0.0027 (8)
C200.0176 (11)0.0172 (12)0.0156 (11)0.0029 (9)0.0016 (9)0.0040 (9)
C210.0189 (11)0.0254 (13)0.0196 (12)0.0044 (10)0.0012 (9)0.0028 (10)
C220.0258 (13)0.0279 (14)0.0164 (12)0.0089 (10)0.0045 (10)0.0060 (10)
C230.0294 (13)0.0188 (13)0.0230 (13)0.0021 (10)0.0045 (10)0.0064 (10)
C240.0198 (11)0.0175 (12)0.0148 (11)0.0011 (9)0.0057 (9)0.0022 (9)
C250.0251 (12)0.0258 (14)0.0183 (12)0.0067 (10)0.0046 (10)0.0060 (10)
C260.0329 (14)0.0376 (16)0.0172 (12)0.0143 (12)0.0046 (11)0.0106 (11)
C270.0465 (17)0.0268 (15)0.0362 (16)0.0020 (12)0.0301 (13)0.0022 (12)
C280.0131 (10)0.0135 (11)0.0163 (11)0.0019 (9)0.0023 (8)0.0015 (9)
C290.0212 (11)0.0178 (12)0.0220 (12)0.0061 (10)0.0023 (9)0.0040 (10)
C300.0147 (11)0.0234 (13)0.0313 (14)0.0009 (10)0.0064 (10)0.0058 (11)
C310.0251 (12)0.0162 (12)0.0255 (13)0.0073 (10)0.0073 (10)0.0025 (10)
Geometric parameters (Å, º) top
Mo1—Cl12.4404 (7)C1—C81.385 (3)
Mo1—Cl5i2.4667 (10)C1—C141.394 (3)
Mo1—Cl42.4692 (7)C1—C21.395 (3)
Mo1—Cl62.4729 (7)C2—C71.396 (3)
Mo1—Cl72.4770 (10)C2—C31.405 (3)
Mo1—Mo22.6047 (5)C3—C41.376 (3)
Mo1—Mo32.6121 (6)C4—C51.407 (3)
Mo1—Mo3i2.6152 (5)C5—C61.413 (3)
Mo1—Mo2i2.6159 (6)C5—C201.532 (3)
Mo2—Cl22.4207 (7)C6—C71.383 (3)
Mo2—Cl52.4631 (8)C8—C91.405 (3)
Mo2—Cl72.4705 (7)C8—C131.408 (3)
Mo2—Cl42.4724 (7)C9—C101.375 (3)
Mo2—Cl6i2.4756 (7)C10—C111.400 (3)
Mo2—Mo3i2.6033 (9)C11—C121.411 (3)
Mo2—Mo32.6124 (5)C11—C241.529 (3)
Mo2—Mo1i2.6159 (6)C12—C131.369 (3)
Mo3—Cl32.4358 (7)C14—C151.402 (3)
Mo3—Cl4i2.4712 (7)C14—C191.405 (3)
Mo3—Cl62.4765 (7)C15—C161.376 (3)
Mo3—Cl72.4770 (8)C16—C171.405 (3)
Mo3—Cl52.4797 (7)C17—C181.407 (3)
Mo3—Mo2i2.6032 (9)C17—C281.532 (3)
Mo3—Mo1i2.6152 (5)C18—C191.377 (3)
Cl4—Mo3i2.4713 (7)C20—C221.535 (3)
Cl5—Mo1i2.4668 (10)C20—C211.541 (3)
Cl6—Mo2i2.4755 (7)C20—C231.542 (3)
O1—C191.382 (3)C24—C251.532 (3)
O1—C31.385 (3)C24—C261.536 (3)
O2—C91.380 (3)C24—C271.535 (3)
O2—C71.382 (3)C28—C311.530 (3)
O3—C151.377 (2)C28—C301.540 (3)
O3—C131.384 (2)C28—C291.539 (3)
Cl1—Mo1—Cl5i92.72 (2)Cl3—Mo3—Mo2136.56 (2)
Cl1—Mo1—Cl490.77 (3)Cl4i—Mo3—Mo2118.04 (2)
Cl5i—Mo1—Cl490.17 (2)Cl6—Mo3—Mo2117.865 (19)
Cl1—Mo1—Cl693.72 (3)Cl7—Mo3—Mo258.01 (2)
Cl5i—Mo1—Cl689.28 (2)Cl5—Mo3—Mo257.785 (18)
Cl4—Mo1—Cl6175.499 (19)Mo2i—Mo3—Mo289.853 (15)
Cl1—Mo1—Cl792.17 (2)Mo1—Mo3—Mo259.808 (16)
Cl5i—Mo1—Cl7175.10 (2)Cl3—Mo3—Mo1i135.07 (2)
Cl4—Mo1—Cl790.05 (2)Cl4i—Mo3—Mo1i58.001 (17)
Cl6—Mo1—Cl790.13 (2)Cl6—Mo3—Mo1i118.13 (2)
Cl1—Mo1—Mo2133.837 (19)Cl7—Mo3—Mo1i118.052 (17)
Cl5i—Mo1—Mo2118.124 (18)Cl5—Mo3—Mo1i57.84 (2)
Cl4—Mo1—Mo258.250 (18)Mo2i—Mo3—Mo1i59.883 (12)
Cl6—Mo1—Mo2118.294 (19)Mo1—Mo3—Mo1i90.106 (16)
Cl7—Mo1—Mo258.113 (16)Mo2—Mo3—Mo1i60.054 (15)
Cl1—Mo1—Mo3135.900 (19)Mo1—Cl4—Mo3i63.92 (2)
Cl5i—Mo1—Mo3117.61 (2)Mo1—Cl4—Mo263.62 (2)
Cl4—Mo1—Mo3118.33 (2)Mo3i—Cl4—Mo263.55 (3)
Cl6—Mo1—Mo358.21 (2)Mo2—Cl5—Mo1i64.10 (2)
Cl7—Mo1—Mo358.18 (2)Mo2—Cl5—Mo363.811 (16)
Mo2—Mo1—Mo360.102 (11)Mo1i—Cl5—Mo363.834 (16)
Cl1—Mo1—Mo3i134.185 (19)Mo1—Cl6—Mo2i63.826 (19)
Cl5i—Mo1—Mo3i58.324 (16)Mo1—Cl6—Mo363.709 (19)
Cl4—Mo1—Mo3i58.078 (19)Mo2i—Cl6—Mo363.43 (2)
Cl6—Mo1—Mo3i118.04 (2)Mo2—Cl7—Mo363.744 (17)
Cl7—Mo1—Mo3i117.925 (19)Mo2—Cl7—Mo163.534 (17)
Mo2—Mo1—Mo3i59.83 (2)Mo3—Cl7—Mo163.64 (2)
Mo3—Mo1—Mo3i89.892 (16)C19—O1—C3120.45 (16)
Cl1—Mo1—Mo2i136.404 (19)C9—O2—C7120.23 (17)
Cl5i—Mo1—Mo2i57.89 (2)C15—O3—C13120.38 (17)
Cl4—Mo1—Mo2i117.98 (2)C8—C1—C14119.9 (2)
Cl6—Mo1—Mo2i58.14 (2)C8—C1—C2120.2 (2)
Cl7—Mo1—Mo2i117.88 (2)C14—C1—C2119.9 (2)
Mo2—Mo1—Mo2i89.745 (14)C7—C2—C1119.4 (2)
Mo3—Mo1—Mo2i59.73 (3)C7—C2—C3120.8 (2)
Mo3i—Mo1—Mo2i59.919 (12)C1—C2—C3119.7 (2)
Cl2—Mo2—Cl592.93 (3)C4—C3—O1120.01 (19)
Cl2—Mo2—Cl790.56 (3)C4—C3—C2120.0 (2)
Cl5—Mo2—Cl790.01 (2)O1—C3—C2120.01 (19)
Cl2—Mo2—Cl491.44 (3)C3—C4—C5119.2 (2)
Cl5—Mo2—Cl4175.623 (19)C4—C5—C6121.1 (2)
Cl7—Mo2—Cl490.12 (2)C4—C5—C20121.44 (19)
Cl2—Mo2—Cl6i93.60 (3)C6—C5—C20117.42 (19)
Cl5—Mo2—Cl6i89.30 (2)C7—C6—C5118.8 (2)
Cl7—Mo2—Cl6i175.811 (19)O2—C7—C6119.49 (19)
Cl4—Mo2—Cl6i90.25 (2)O2—C7—C2120.41 (19)
Cl2—Mo2—Mo3i135.33 (2)C6—C7—C2120.1 (2)
Cl5—Mo2—Mo3i118.07 (2)C1—C8—C9119.8 (2)
Cl7—Mo2—Mo3i118.618 (18)C1—C8—C13120.2 (2)
Cl4—Mo2—Mo3i58.20 (2)C9—C8—C13120.04 (19)
Cl6i—Mo2—Mo3i58.302 (17)C10—C9—O2120.18 (19)
Cl2—Mo2—Mo1133.25 (2)C10—C9—C8119.8 (2)
Cl5—Mo2—Mo1118.477 (17)O2—C9—C8119.97 (19)
Cl7—Mo2—Mo158.35 (2)C9—C10—C11119.6 (2)
Cl4—Mo2—Mo158.132 (16)C10—C11—C12121.06 (19)
Cl6i—Mo2—Mo1118.57 (2)C10—C11—C24120.83 (19)
Mo3i—Mo2—Mo160.284 (11)C12—C11—C24118.01 (19)
Cl2—Mo2—Mo3134.48 (2)C13—C12—C11118.9 (2)
Cl5—Mo2—Mo358.40 (2)C12—C13—O3119.94 (19)
Cl7—Mo2—Mo358.249 (18)C12—C13—C8120.53 (19)
Cl4—Mo2—Mo3118.20 (2)O3—C13—C8119.53 (19)
Cl6i—Mo2—Mo3118.05 (2)C1—C14—C15119.54 (19)
Mo3i—Mo2—Mo390.145 (15)C1—C14—C19119.8 (2)
Mo1—Mo2—Mo360.090 (14)C15—C14—C19120.62 (19)
Cl2—Mo2—Mo1i136.49 (2)C16—C15—O3119.88 (19)
Cl5—Mo2—Mo1i58.02 (3)C16—C15—C14119.67 (19)
Cl7—Mo2—Mo1i118.266 (17)O3—C15—C14120.44 (18)
Cl4—Mo2—Mo1i118.25 (3)C15—C16—C17119.8 (2)
Cl6i—Mo2—Mo1i58.037 (16)C16—C17—C18120.6 (2)
Mo3i—Mo2—Mo1i60.061 (18)C16—C17—C28118.79 (19)
Mo1—Mo2—Mo1i90.254 (15)C18—C17—C28120.54 (19)
Mo3—Mo2—Mo1i60.026 (17)C19—C18—C17119.5 (2)
Cl3—Mo3—Cl4i91.30 (3)C18—C19—O1120.16 (19)
Cl3—Mo3—Cl691.24 (3)C18—C19—C14119.8 (2)
Cl4i—Mo3—Cl690.25 (2)O1—C19—C14120.00 (19)
Cl3—Mo3—Cl793.20 (3)C5—C20—C22112.26 (18)
Cl4i—Mo3—Cl7175.481 (19)C5—C20—C21108.31 (18)
Cl6—Mo3—Cl790.05 (2)C22—C20—C21109.96 (19)
Cl3—Mo3—Cl593.90 (2)C5—C20—C23108.90 (19)
Cl4i—Mo3—Cl589.82 (2)C22—C20—C23108.21 (19)
Cl6—Mo3—Cl5174.856 (18)C21—C20—C23109.15 (19)
Cl7—Mo3—Cl589.48 (2)C11—C24—C25112.46 (19)
Cl3—Mo3—Mo2i133.59 (2)C11—C24—C26110.38 (18)
Cl4i—Mo3—Mo2i58.24 (2)C25—C24—C26108.61 (19)
Cl6—Mo3—Mo2i58.267 (17)C11—C24—C27106.19 (19)
Cl7—Mo3—Mo2i118.36 (2)C25—C24—C27109.1 (2)
Cl5—Mo3—Mo2i117.694 (17)C26—C24—C27110.1 (2)
Cl3—Mo3—Mo1134.789 (19)C31—C28—C17110.95 (18)
Cl4i—Mo3—Mo1118.43 (3)C31—C28—C30108.21 (19)
Cl6—Mo3—Mo158.078 (16)C17—C28—C30107.06 (18)
Cl7—Mo3—Mo158.18 (3)C31—C28—C29108.57 (19)
Cl5—Mo3—Mo1117.576 (17)C17—C28—C29111.69 (18)
Mo2i—Mo3—Mo160.21 (2)C30—C28—C29110.29 (19)
Symmetry code: (i) x+2, y+2, z.
(6160K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.752 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.26 mm1
a = 12.964 (2) ÅT = 160 K
c = 16.813 (3) ÅPrism, orange
V = 2447.3 (7) Å30.25 × 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 tubeRint = 0.052
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8102 measured reflectionsk = 1516
561 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.04Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
561 reflections(Δ/σ)max = 0.007
47 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0292 (3)
F10.04964 (11)0.11613 (9)0.05494 (6)0.0436 (4)
O10.78529 (13)0.00000.25000.0366 (5)
C11.00000.00000.25000.0262 (9)
C21.00000.1072 (2)0.25000.0293 (6)
C30.8916 (2)0.1065 (2)0.25166 (9)0.0317 (4)
C40.8909 (2)0.2123 (2)0.25376 (10)0.0410 (5)
H40.81990.21360.25760.049*
C51.00000.3171 (2)0.25000.0439 (8)
H51.00000.38880.25000.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0277 (4)0.0277 (4)0.0323 (6)0.0138 (2)0.0000.000
F10.0444 (7)0.0351 (7)0.0492 (7)0.0183 (6)0.0053 (5)0.0117 (5)
O10.0324 (7)0.0458 (11)0.0360 (10)0.0229 (6)0.0012 (4)0.0025 (9)
C10.0296 (13)0.0296 (13)0.020 (2)0.0148 (7)0.0000.000
C20.0348 (14)0.0317 (10)0.0226 (11)0.0174 (7)0.0004 (10)0.0002 (5)
C30.0374 (11)0.0357 (11)0.0249 (8)0.0204 (9)0.0006 (7)0.0007 (7)
C40.0561 (13)0.0514 (13)0.0312 (10)0.0387 (11)0.0043 (9)0.0037 (9)
C50.071 (2)0.0389 (11)0.0324 (14)0.0357 (11)0.0084 (14)0.0042 (7)
Geometric parameters (Å, º) top
P1—F1i1.6017 (10)C1—C2vii1.390 (3)
P1—F11.6017 (10)C1—C21.390 (3)
P1—F1ii1.6017 (10)C1—C2viii1.390 (3)
P1—F1iii1.6017 (10)C2—C3ix1.401 (2)
P1—F1iv1.6017 (10)C2—C31.401 (2)
P1—F1v1.6017 (10)C3—C41.378 (3)
O1—C31.380 (2)C4—C51.389 (2)
O1—C3vi1.380 (2)C5—C4ix1.389 (2)
F1i—P1—F1180.0F1iv—P1—F1v89.94 (6)
F1i—P1—F1ii89.94 (6)C3—O1—C3vi120.2 (2)
F1—P1—F1ii90.06 (6)C2vii—C1—C2120.0
F1i—P1—F1iii90.06 (6)C2vii—C1—C2viii120.0
F1—P1—F1iii89.94 (6)C2—C1—C2viii120.0
F1ii—P1—F1iii89.94 (6)C1—C2—C3ix119.65 (13)
F1i—P1—F1iv89.94 (6)C1—C2—C3119.65 (13)
F1—P1—F1iv90.06 (6)C3ix—C2—C3120.7 (3)
F1ii—P1—F1iv90.06 (6)O1—C3—C4119.7 (2)
F1iii—P1—F1iv180.0O1—C3—C2120.2 (2)
F1i—P1—F1v90.06 (6)C4—C3—C2120.0 (2)
F1—P1—F1v89.94 (6)C3—C4—C5117.5 (2)
F1ii—P1—F1v180.0C4—C5—C4ix124.1 (3)
F1iii—P1—F1v90.06 (6)
Symmetry codes: (i) x, y, z; (ii) y, xy, z; (iii) xy, x, z; (iv) x+y, x, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6198K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.740 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 12.997 (2) ÅT = 198 K
c = 16.843 (3) ÅPrism, orange
V = 2464.0 (7) Å30.25 × 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 tubeRint = 0.057
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8165 measured reflectionsk = 1615
566 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.06Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
566 reflections(Δ/σ)max = 0.011
47 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0373 (4)
F10.04949 (12)0.11560 (11)0.05468 (7)0.0551 (5)
O10.7863 (2)0.00000.25000.0461 (6)
C11.00000.00000.25000.0333 (10)
C21.00000.1068 (2)0.25000.0367 (7)
C30.8922 (2)0.1066 (2)0.25163 (10)0.0402 (5)
C40.8914 (2)0.2119 (2)0.25372 (12)0.0519 (6)
H40.82060.21310.25750.062*
C51.00000.3163 (2)0.25000.0556 (10)
H51.00000.38780.25000.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0361 (5)0.0361 (5)0.0397 (7)0.0180 (2)0.0000.000
F10.0564 (9)0.0450 (8)0.0602 (9)0.0226 (7)0.0068 (7)0.0151 (6)
O10.0426 (9)0.0588 (14)0.0423 (12)0.0294 (7)0.0011 (5)0.0022 (10)
C10.038 (2)0.038 (2)0.024 (2)0.0189 (8)0.0000.000
C20.043 (2)0.0397 (12)0.0286 (13)0.0215 (9)0.0006 (13)0.0003 (6)
C30.0495 (14)0.0460 (13)0.0309 (10)0.0283 (11)0.0004 (9)0.0012 (9)
C40.072 (2)0.066 (2)0.0385 (12)0.0503 (15)0.0041 (12)0.0035 (12)
C50.091 (3)0.0497 (13)0.040 (2)0.0453 (15)0.013 (2)0.0063 (9)
Geometric parameters (Å, º) top
P1—F11.5977 (12)C1—C2vii1.388 (3)
P1—F1i1.5977 (12)C1—C2viii1.388 (3)
P1—F1ii1.5977 (12)C1—C21.388 (3)
P1—F1iii1.5977 (12)C2—C3ix1.400 (2)
P1—F1iv1.5977 (12)C2—C31.400 (2)
P1—F1v1.5977 (12)C3—C41.374 (3)
O1—C31.381 (2)C4—C51.386 (3)
O1—C3vi1.381 (2)C5—C4ix1.386 (3)
F1—P1—F1i89.91 (7)F1iv—P1—F1v180.0
F1—P1—F1ii180.0C3—O1—C3vi120.6 (2)
F1i—P1—F1ii90.09 (7)C2vii—C1—C2viii120.0
F1—P1—F1iii90.09 (7)C2vii—C1—C2120.0
F1i—P1—F1iii180.0C2viii—C1—C2120.0
F1ii—P1—F1iii89.91 (7)C1—C2—C3ix119.90 (15)
F1—P1—F1iv89.91 (7)C1—C2—C3119.90 (15)
F1i—P1—F1iv90.09 (7)C3ix—C2—C3120.2 (3)
F1ii—P1—F1iv90.09 (7)C4—C3—O1120.0 (2)
F1iii—P1—F1iv89.91 (7)C4—C3—C2120.3 (3)
F1—P1—F1v90.09 (7)O1—C3—C2119.7 (2)
F1i—P1—F1v89.91 (7)C3—C4—C5117.6 (2)
F1ii—P1—F1v89.91 (7)C4—C5—C4ix124.0 (3)
F1iii—P1—F1v90.09 (7)
Symmetry codes: (i) xy, x, z; (ii) x, y, z; (iii) x+y, x, z; (iv) y, x+y, z; (v) y, xy, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6220K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.733 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 13.015 (2) ÅT = 220 K
c = 16.859 (3) ÅPrism, orange
V = 2473.3 (7) Å30.25 × 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 tubeRint = 0.057
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8196 measured reflectionsk = 1616
567 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.02Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
566 reflections(Δ/σ)max = 0.010
47 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0413 (4)
F10.04933 (13)0.11536 (11)0.05450 (8)0.0619 (5)
O10.7865 (2)0.00000.25000.0518 (6)
C11.00000.00000.25000.0371 (10)
C21.00000.1068 (2)0.25000.0408 (7)
C30.8922 (2)0.1062 (2)0.25163 (11)0.0452 (5)
C40.8916 (2)0.2113 (2)0.25375 (12)0.0583 (7)
H40.82090.21250.25760.070*
C51.00000.3157 (3)0.25000.0639 (11)
H51.00000.38720.25000.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0400 (5)0.0400 (5)0.0440 (7)0.0200 (2)0.0000.000
F10.0641 (9)0.0507 (8)0.0674 (9)0.0261 (7)0.0070 (7)0.0167 (6)
O10.0466 (9)0.067 (2)0.0484 (12)0.0337 (8)0.0019 (6)0.0037 (11)
C10.042 (2)0.042 (2)0.027 (2)0.0212 (8)0.0000.000
C20.049 (2)0.0452 (12)0.0296 (13)0.0244 (9)0.0009 (13)0.0004 (7)
C30.0550 (15)0.0521 (14)0.0347 (10)0.0315 (11)0.0003 (10)0.0010 (10)
C40.083 (2)0.073 (2)0.0432 (12)0.057 (2)0.0062 (13)0.0048 (12)
C50.104 (3)0.0553 (14)0.049 (2)0.052 (2)0.015 (2)0.0076 (10)
Geometric parameters (Å, º) top
P1—F11.5959 (12)C1—C2vii1.391 (3)
P1—F1i1.5959 (12)C1—C21.391 (3)
P1—F1ii1.5959 (12)C1—C2viii1.391 (3)
P1—F1iii1.5959 (12)C2—C3ix1.399 (2)
P1—F1iv1.5959 (12)C2—C31.399 (2)
P1—F1v1.5959 (12)C3—C41.373 (3)
O1—C31.379 (3)C4—C51.387 (3)
O1—C3vi1.379 (3)C5—C4ix1.387 (3)
F1—P1—F1i89.84 (7)F1iv—P1—F1v180.0
F1—P1—F1ii90.16 (7)C3—O1—C3vi120.5 (2)
F1i—P1—F1ii180.0C2vii—C1—C2120.0
F1—P1—F1iii180.0C2vii—C1—C2viii120.0
F1i—P1—F1iii90.16 (7)C2—C1—C2viii120.0
F1ii—P1—F1iii89.84 (7)C1—C2—C3ix119.7 (2)
F1—P1—F1iv90.16 (7)C1—C2—C3119.7 (2)
F1i—P1—F1iv89.84 (7)C3ix—C2—C3120.7 (3)
F1ii—P1—F1iv90.16 (7)C4—C3—O1119.9 (2)
F1iii—P1—F1iv89.84 (7)C4—C3—C2120.0 (3)
F1—P1—F1v89.84 (7)O1—C3—C2120.1 (2)
F1i—P1—F1v90.16 (7)C3—C4—C5117.7 (3)
F1ii—P1—F1v89.84 (7)C4—C5—C4ix123.8 (3)
F1iii—P1—F1v90.16 (7)
Symmetry codes: (i) xy, x, z; (ii) x+y, x, z; (iii) x, y, z; (iv) y, xy, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6243K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.724 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 13.040 (2) ÅT = 243 K
c = 16.884 (3) ÅPrism, orange
V = 2486.5 (7) Å30.25 × 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 tubeRint = 0.061
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8207 measured reflectionsk = 1615
569 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 0.95Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
569 reflections(Δ/σ)max = 0.023
47 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0470 (4)
F10.04927 (13)0.11510 (11)0.05442 (8)0.0707 (5)
O10.7870 (2)0.00000.25000.0589 (6)
C11.00000.00000.25000.0402 (10)
C21.00000.1067 (2)0.25000.0463 (7)
C30.8924 (2)0.1059 (2)0.25163 (11)0.0518 (6)
C40.8918 (2)0.2111 (2)0.25370 (12)0.0664 (7)
H40.82140.21260.25740.080*
C51.00000.3145 (3)0.25000.0711 (11)
H51.00000.38580.25000.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0463 (5)0.0463 (5)0.0484 (7)0.0231 (2)0.0000.000
F10.0743 (10)0.0576 (8)0.0751 (10)0.0292 (8)0.0084 (7)0.0195 (6)
O10.0533 (9)0.076 (2)0.0554 (13)0.0378 (8)0.0018 (6)0.0036 (12)
C10.046 (2)0.046 (2)0.029 (2)0.0229 (8)0.0000.000
C20.056 (2)0.0509 (13)0.0334 (13)0.0281 (9)0.0022 (14)0.0011 (7)
C30.061 (2)0.0635 (15)0.0388 (10)0.0375 (12)0.0001 (11)0.0008 (10)
C40.092 (2)0.085 (2)0.0501 (13)0.065 (2)0.0075 (13)0.0068 (13)
C50.118 (4)0.0630 (15)0.051 (2)0.059 (2)0.018 (2)0.0091 (10)
Geometric parameters (Å, º) top
P1—F11.5954 (12)C1—C2vii1.391 (3)
P1—F1i1.5954 (12)C1—C21.391 (3)
P1—F1ii1.5954 (12)C1—C2viii1.391 (3)
P1—F1iii1.5954 (12)C2—C3ix1.398 (2)
P1—F1iv1.5954 (12)C2—C31.398 (2)
P1—F1v1.5954 (12)C3—C41.377 (3)
O1—C3vi1.377 (3)C4—C51.382 (3)
O1—C31.377 (3)C5—C4ix1.382 (3)
F1—P1—F1i180.0F1iv—P1—F1v90.14 (7)
F1—P1—F1ii90.14 (7)C3vi—O1—C3120.5 (2)
F1i—P1—F1ii89.86 (7)C2vii—C1—C2120.0
F1—P1—F1iii90.14 (7)C2vii—C1—C2viii120.0
F1i—P1—F1iii89.86 (7)C2—C1—C2viii120.0
F1ii—P1—F1iii90.14 (7)C1—C2—C3ix119.6 (2)
F1—P1—F1iv89.86 (7)C1—C2—C3119.6 (2)
F1i—P1—F1iv90.14 (7)C3ix—C2—C3120.8 (3)
F1ii—P1—F1iv180.0C4—C3—O1120.0 (2)
F1iii—P1—F1iv89.86 (7)C4—C3—C2119.9 (3)
F1—P1—F1v89.86 (7)O1—C3—C2120.1 (2)
F1i—P1—F1v90.14 (7)C3—C4—C5117.3 (3)
F1ii—P1—F1v89.86 (7)C4—C5—C4ix124.6 (3)
F1iii—P1—F1v180.0
Symmetry codes: (i) x, y, z; (ii) x+y, x, z; (iii) y, xy, z; (iv) xy, x, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6268K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.714 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 13.067 (2) ÅT = 268 K
c = 16.910 (3) ÅPrism, orange
V = 2500.4 (7) Å30.25 × 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 tubeRint = 0.062
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8252 measured reflectionsk = 1616
572 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.07Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
571 reflections(Δ/σ)max = 0.040
47 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0530 (5)
F10.0491 (2)0.11466 (13)0.05418 (9)0.0801 (6)
O10.7875 (2)0.00000.25000.0667 (8)
C11.00000.00000.25000.0453 (13)
C21.00000.1064 (3)0.25000.0516 (8)
C30.8925 (3)0.1056 (3)0.25161 (13)0.0579 (7)
C40.8923 (3)0.2108 (3)0.25373 (15)0.0753 (9)
H40.82210.21220.25750.090*
C51.00000.3140 (3)0.25000.0819 (14)
H51.00000.38520.25000.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0520 (6)0.0520 (6)0.0549 (9)0.0260 (3)0.0000.000
F10.0858 (13)0.0642 (10)0.0849 (12)0.0334 (10)0.0104 (9)0.0231 (8)
O10.0609 (12)0.087 (2)0.061 (2)0.0435 (10)0.0021 (7)0.0041 (15)
C10.052 (2)0.052 (2)0.033 (3)0.0258 (10)0.0000.000
C20.060 (2)0.056 (2)0.040 (2)0.0301 (11)0.003 (2)0.0016 (9)
C30.069 (2)0.070 (2)0.0436 (13)0.041 (2)0.0010 (13)0.0001 (13)
C40.107 (3)0.097 (2)0.055 (2)0.075 (2)0.008 (2)0.006 (2)
C50.133 (5)0.073 (2)0.060 (2)0.067 (2)0.019 (3)0.0093 (14)
Geometric parameters (Å, º) top
P1—F1i1.5920 (14)C1—C2vii1.390 (4)
P1—F11.5920 (14)C1—C2viii1.390 (4)
P1—F1ii1.5920 (14)C1—C21.390 (4)
P1—F1iii1.5920 (14)C2—C3ix1.400 (3)
P1—F1iv1.5920 (14)C2—C31.400 (3)
P1—F1v1.5920 (14)C3—C41.376 (4)
O1—C31.377 (3)C4—C51.380 (4)
O1—C3vi1.377 (3)C5—C4ix1.380 (4)
F1i—P1—F1180.0F1iv—P1—F1v90.18 (8)
F1i—P1—F1ii89.82 (8)C3—O1—C3vi120.6 (3)
F1—P1—F1ii90.18 (8)C2vii—C1—C2viii120.0
F1i—P1—F1iii89.82 (8)C2vii—C1—C2120.0
F1—P1—F1iii90.18 (8)C2viii—C1—C2120.0
F1ii—P1—F1iii90.18 (8)C1—C2—C3ix119.6 (2)
F1i—P1—F1iv90.18 (8)C1—C2—C3119.6 (2)
F1—P1—F1iv89.82 (8)C3ix—C2—C3120.7 (4)
F1ii—P1—F1iv180.0C4—C3—O1120.2 (3)
F1iii—P1—F1iv89.82 (8)C4—C3—C2119.8 (3)
F1i—P1—F1v90.18 (8)O1—C3—C2120.0 (3)
F1—P1—F1v89.82 (8)C3—C4—C5117.7 (3)
F1ii—P1—F1v89.82 (8)C4—C5—C4ix124.2 (4)
F1iii—P1—F1v180.0
Symmetry codes: (i) x, y, z; (ii) x+y, x, z; (iii) y, xy, z; (iv) xy, x, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6293K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.705 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 13.094 (2) ÅT = 293 K
c = 16.937 (3) ÅPrism, orange
V = 2514.7 (7) Å30.25 × 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 tubeRint = 0.067
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8328 measured reflectionsk = 1616
575 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.00Calculated w = 1/[σ2(Fo2) + (0.0456P)2 + 2.6625P]
where P = (Fo2 + 2Fc2)/3
575 reflections(Δ/σ)max = 0.022
47 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.17 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0599 (5)
F10.0488 (2)0.11413 (13)0.05407 (9)0.0905 (7)
O10.7880 (2)0.00000.25000.0746 (8)
C11.00000.00000.25000.0516 (14)
C21.00000.1061 (3)0.25000.0584 (9)
C30.8929 (3)0.1055 (3)0.25153 (13)0.0652 (7)
C40.8928 (3)0.2105 (3)0.2535 (2)0.0848 (10)
H40.82270.21190.25720.102*
C51.00000.3134 (3)0.25000.095 (2)
H51.00000.38440.25000.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0593 (7)0.0593 (7)0.0611 (10)0.0297 (3)0.0000.000
F10.0974 (14)0.0744 (11)0.0948 (13)0.0393 (11)0.0108 (10)0.0257 (8)
O10.0682 (12)0.099 (2)0.067 (2)0.0493 (11)0.0020 (8)0.004 (2)
C10.058 (2)0.058 (2)0.039 (3)0.0289 (11)0.0000.000
C20.070 (3)0.064 (2)0.044 (2)0.0348 (13)0.001 (2)0.0003 (9)
C30.079 (2)0.078 (2)0.0484 (14)0.047 (2)0.002 (2)0.0001 (15)
C40.119 (3)0.110 (3)0.062 (2)0.085 (2)0.011 (2)0.010 (2)
C50.157 (5)0.084 (2)0.067 (3)0.079 (3)0.024 (3)0.012 (2)
Geometric parameters (Å, º) top
P1—F1i1.5891 (14)C1—C2vii1.390 (4)
P1—F1ii1.5891 (14)C1—C2viii1.390 (4)
P1—F11.5891 (14)C1—C21.390 (4)
P1—F1iii1.5891 (14)C2—C3ix1.398 (3)
P1—F1iv1.5891 (14)C2—C31.398 (3)
P1—F1v1.5891 (14)C3—C41.375 (4)
O1—C31.378 (3)C4—C51.378 (4)
O1—C3vi1.378 (3)C5—C4ix1.378 (4)
F1i—P1—F1ii90.11 (8)F1iv—P1—F1v180.0
F1i—P1—F1180.0C3—O1—C3vi120.6 (3)
F1ii—P1—F189.89 (8)C2vii—C1—C2viii120.0
F1i—P1—F1iii89.89 (8)C2vii—C1—C2120.0
F1ii—P1—F1iii180.0C2viii—C1—C2120.0
F1—P1—F1iii90.11 (8)C1—C2—C3ix119.7 (2)
F1i—P1—F1iv90.11 (8)C1—C2—C3119.7 (2)
F1ii—P1—F1iv90.11 (8)C3ix—C2—C3120.6 (4)
F1—P1—F1iv89.89 (8)C4—C3—O1120.3 (3)
F1iii—P1—F1iv89.89 (8)C4—C3—C2119.8 (4)
F1i—P1—F1v89.89 (8)O1—C3—C2120.0 (3)
F1ii—P1—F1v89.89 (8)C3—C4—C5117.9 (4)
F1—P1—F1v90.11 (8)C4—C5—C4ix124.0 (4)
F1iii—P1—F1v90.11 (8)
Symmetry codes: (i) x, y, z; (ii) xy, x, z; (iii) x+y, x, z; (iv) y, x+y, z; (v) y, xy, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6313K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.699 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 13.111 (2) ÅT = 313 K
c = 16.953 (3) ÅPrism, orange
V = 2523.6 (7) Å30.25 × 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 tubeRint = 0.067
Graphite monochromatorθmax = 26.3°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8369 measured reflectionsk = 1616
577 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.05Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 1.2721P]
where P = (Fo2 + 2Fc2)/3
576 reflections(Δ/σ)max = 0.003
47 parametersΔρmax = 0.10 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0643 (5)
F10.0486 (2)0.11406 (13)0.05391 (9)0.0998 (7)
O10.7886 (2)0.00000.25000.0808 (8)
C11.00000.00000.25000.0555 (13)
C21.00000.1063 (3)0.25000.0626 (9)
C30.8930 (3)0.1053 (3)0.25162 (12)0.0711 (7)
C40.8923 (3)0.2093 (3)0.25351 (15)0.0934 (10)
H40.82220.21060.25700.112*
C51.00000.3127 (3)0.25000.104 (2)
H51.00000.38360.25000.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0634 (7)0.0634 (7)0.0662 (9)0.0317 (3)0.0000.000
F10.1059 (14)0.0818 (11)0.1048 (13)0.0418 (11)0.0121 (10)0.0294 (8)
O10.0744 (12)0.106 (2)0.073 (2)0.0529 (11)0.0009 (8)0.002 (2)
C10.064 (2)0.064 (2)0.038 (3)0.0321 (11)0.0000.000
C20.077 (3)0.068 (2)0.046 (2)0.0386 (13)0.001 (2)0.0006 (9)
C30.089 (2)0.088 (2)0.0513 (13)0.055 (2)0.004 (2)0.0010 (14)
C40.133 (3)0.120 (3)0.067 (2)0.093 (2)0.009 (2)0.009 (2)
C50.172 (5)0.093 (2)0.073 (3)0.086 (3)0.027 (3)0.013 (2)
Geometric parameters (Å, º) top
P1—F1i1.5889 (14)C1—C2vii1.394 (4)
P1—F11.5889 (14)C1—C21.394 (4)
P1—F1ii1.5889 (14)C1—C2viii1.394 (4)
P1—F1iii1.5889 (14)C2—C3ix1.397 (3)
P1—F1iv1.5889 (14)C2—C31.397 (3)
P1—F1v1.5889 (14)C3—C41.369 (4)
O1—C31.375 (3)C4—C51.385 (4)
O1—C3vi1.375 (3)C5—C4ix1.385 (4)
F1i—P1—F1180.0F1iv—P1—F1v180.0
F1i—P1—F1ii90.21 (8)C3—O1—C3vi120.9 (3)
F1—P1—F1ii89.79 (8)C2vii—C1—C2120.0
F1i—P1—F1iii89.79 (8)C2vii—C1—C2viii120.0
F1—P1—F1iii90.21 (8)C2—C1—C2viii120.000 (1)
F1ii—P1—F1iii180.0C1—C2—C3ix119.5 (2)
F1i—P1—F1iv89.79 (8)C1—C2—C3119.5 (2)
F1—P1—F1iv90.21 (8)C3ix—C2—C3120.9 (4)
F1ii—P1—F1iv89.79 (8)C4—C3—O1120.1 (3)
F1iii—P1—F1iv90.21 (8)C4—C3—C2119.9 (4)
F1i—P1—F1v90.21 (8)O1—C3—C2120.0 (3)
F1—P1—F1v89.79 (8)C3—C4—C5117.6 (4)
F1ii—P1—F1v90.21 (8)C4—C5—C4ix124.1 (4)
F1iii—P1—F1v89.79 (8)
Symmetry codes: (i) x, y, z; (ii) xy, x, z; (iii) x+y, x, z; (iv) y, xy, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6338K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.692 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.25 mm1
a = 13.131 (2) ÅT = 338 K
c = 16.970 (3) ÅPrism, orange
V = 2534.0 (7) Å30.25 × 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 tubeRint = 0.071
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8356 measured reflectionsk = 1615
579 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.05Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 1.2721P]
where P = (Fo2 + 2Fc2)/3
579 reflections(Δ/σ)max = 0.028
47 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.12 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0720 (6)
F10.0483 (2)0.11356 (14)0.05367 (9)0.1126 (8)
O10.7892 (2)0.00000.25000.0917 (9)
C11.00000.00000.25000.0620 (15)
C21.00000.1056 (3)0.25000.0688 (10)
C30.8935 (3)0.1050 (3)0.25159 (13)0.0800 (8)
C40.8925 (3)0.2090 (4)0.2537 (2)0.1036 (12)
H40.82260.21040.25740.124*
C51.00000.3114 (4)0.25000.117 (2)
H51.00000.38220.25000.140*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0726 (8)0.0726 (8)0.0708 (10)0.0363 (4)0.0000.000
F10.121 (2)0.0923 (12)0.1163 (15)0.0475 (13)0.0134 (11)0.0324 (9)
O10.0845 (14)0.122 (3)0.081 (2)0.0611 (14)0.0011 (10)0.002 (2)
C10.071 (2)0.071 (2)0.045 (3)0.0353 (12)0.0000.000
C20.082 (3)0.075 (2)0.051 (2)0.0411 (14)0.002 (2)0.0010 (10)
C30.101 (3)0.098 (3)0.0561 (15)0.060 (2)0.000 (2)0.001 (2)
C40.147 (4)0.132 (3)0.075 (2)0.102 (3)0.011 (2)0.012 (2)
C50.196 (7)0.105 (2)0.079 (3)0.098 (3)0.030 (4)0.015 (2)
Geometric parameters (Å, º) top
P1—F1i1.584 (2)C1—C2vii1.387 (4)
P1—F11.584 (2)C1—C21.387 (4)
P1—F1ii1.584 (2)C1—C2viii1.387 (4)
P1—F1iii1.584 (2)C2—C3ix1.394 (3)
P1—F1iv1.584 (2)C2—C31.394 (3)
P1—F1v1.584 (2)C3—C41.373 (4)
O1—C3vi1.374 (4)C4—C51.381 (4)
O1—C31.374 (4)C5—C4ix1.381 (4)
F1i—P1—F1180.0F1iv—P1—F1v89.76 (9)
F1i—P1—F1ii90.24 (9)C3vi—O1—C3120.6 (3)
F1—P1—F1ii89.76 (9)C2vii—C1—C2120.0
F1i—P1—F1iii89.76 (9)C2vii—C1—C2viii120.0
F1—P1—F1iii90.24 (9)C2—C1—C2viii120.000 (1)
F1ii—P1—F1iii89.76 (9)C1—C2—C3ix119.7 (2)
F1i—P1—F1iv89.76 (9)C1—C2—C3119.7 (2)
F1—P1—F1iv90.24 (9)C3ix—C2—C3120.6 (5)
F1ii—P1—F1iv180.0C4—C3—O1119.8 (3)
F1iii—P1—F1iv90.24 (9)C4—C3—C2120.2 (4)
F1i—P1—F1v90.24 (9)O1—C3—C2120.0 (3)
F1—P1—F1v89.76 (9)C3—C4—C5117.0 (4)
F1ii—P1—F1v90.24 (9)C4—C5—C4ix124.8 (5)
F1iii—P1—F1v180.0
Symmetry codes: (i) x, y, z; (ii) xy, x, z; (iii) y, xy, z; (iv) x+y, x, z; (v) y, x+y, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
(6373K) 4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium hexafluorophosphate top
Crystal data top
C19H9O3·F6PF(000) = 1296
Mr = 430.23Dx = 1.673 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3 2"cµ = 0.24 mm1
a = 13.181 (2) ÅT = 373 K
c = 17.025 (3) ÅPrism, orange
V = 2561.6 (7) Å30.25 × 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 tubeRint = 0.080
Graphite monochromatorθmax = 26.3°, θmin = 3.0°
ω scan, frame data integrationh = 1616
8443 measured reflectionsk = 1615
586 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.09Calculated w = 1/[σ2(Fo2) + (0.0454P)2 + 1.2721P]
where P = (Fo2 + 2Fc2)/3
586 reflections(Δ/σ)max = 0.078
47 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.10 e Å3
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
xyzUiso*/Ueq
P10.00000.00000.00000.0833 (7)
F10.0478 (2)0.1127 (2)0.05332 (11)0.1329 (10)
O10.7903 (2)0.00000.25000.1058 (11)
C11.00000.00000.25000.073 (2)
C21.00000.1046 (4)0.25000.0798 (12)
C30.8941 (4)0.1048 (4)0.25148 (15)0.0943 (10)
C40.8933 (4)0.2087 (4)0.2532 (2)0.124 (2)
H40.82360.21010.25640.149*
C51.00000.3105 (5)0.25000.141 (3)
H51.00000.38110.25000.169*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0845 (9)0.0845 (9)0.0810 (12)0.0422 (5)0.0000.000
F10.143 (2)0.1106 (14)0.135 (2)0.056 (2)0.0130 (14)0.0392 (11)
O10.098 (2)0.142 (3)0.092 (2)0.071 (2)0.0005 (12)0.001 (2)
C10.083 (3)0.083 (3)0.053 (4)0.0417 (14)0.0000.000
C20.090 (3)0.087 (2)0.063 (2)0.045 (2)0.000 (2)0.0001 (12)
C30.121 (4)0.113 (3)0.065 (2)0.070 (3)0.003 (2)0.000 (2)
C40.184 (5)0.157 (4)0.088 (2)0.128 (4)0.020 (3)0.017 (3)
C50.247 (10)0.128 (3)0.088 (4)0.124 (5)0.039 (6)0.019 (3)
Geometric parameters (Å, º) top
P1—F1i1.579 (2)C1—C2vii1.379 (5)
P1—F11.579 (2)C1—C2viii1.379 (5)
P1—F1ii1.579 (2)C1—C21.379 (5)
P1—F1iii1.579 (2)C2—C3ix1.398 (4)
P1—F1iv1.579 (2)C2—C31.398 (4)
P1—F1v1.579 (2)C3—C41.375 (5)
O1—C3vi1.375 (4)C4—C51.376 (5)
O1—C31.375 (4)C5—C4ix1.376 (5)
F1i—P1—F1180.0F1iv—P1—F1v90.24 (10)
F1i—P1—F1ii90.24 (10)C3vi—O1—C3121.0 (4)
F1—P1—F1ii89.76 (10)C2vii—C1—C2viii120.0
F1i—P1—F1iii90.24 (10)C2vii—C1—C2120.0
F1—P1—F1iii89.76 (10)C2viii—C1—C2120.000 (1)
F1ii—P1—F1iii90.24 (10)C1—C2—C3ix120.1 (3)
F1i—P1—F1iv89.76 (10)C1—C2—C3120.1 (3)
F1—P1—F1iv90.24 (10)C3ix—C2—C3119.8 (6)
F1ii—P1—F1iv89.76 (10)C4—C3—O1120.1 (4)
F1iii—P1—F1iv180.0C4—C3—C2120.5 (5)
F1i—P1—F1v89.76 (10)O1—C3—C2119.4 (4)
F1—P1—F1v90.24 (10)C3—C4—C5117.2 (6)
F1ii—P1—F1v180.0C4—C5—C4ix124.7 (7)
F1iii—P1—F1v89.76 (10)
Symmetry codes: (i) x, y, z; (ii) xy, x, z; (iii) y, x+y, z; (iv) y, xy, z; (v) x+y, x, z; (vi) xy, y, z+1/2; (vii) y+1, xy1, z; (viii) x+y+2, x+1, z; (ix) x+2, x+y+1, z+1/2.
 
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