In the title compound, C
21H
14Br
2NO
2+·CF
3O
3S
−, adjacent cations are oriented either parallel or antiparallel. Together with the CF
3O
3S
− anions, the antiparallel-oriented cations form layers in which the ions are linked
via a network of C—H
O (O from the anions) and π–π interactions (between the benzene rings). These layers, in turn, are linked
via a network of five multidirectional π–π interactions between the acridine rings, and the crystal structure is stabilized by electrostatic interactions between the ions. The acridine and independent benzene rings are mutually oriented at an angle of 35.9 (3)°.
Supporting information
CCDC reference: 277767
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.009 Å
- R factor = 0.046
- wR factor = 0.123
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT412_ALERT_2_B Short Intra XH3 .. XHn H4 .. H26D .. 1.72 Ang.
PLAT412_ALERT_2_B Short Intra XH3 .. XHn H5 .. H26A .. 1.78 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for Br25 - C23 .. 5.80 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S27
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KM-4 Software (Kuma Diffraction, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
9-(2,6-Dibromophenoxycarbonyl)-10-methylacridinium trifluoromethanesulfonate
top
Crystal data top
C21H14Br2NO2+·CF3O3S− | Z = 2 |
Mr = 621.21 | F(000) = 612 |
Triclinic, P1 | Dx = 1.869 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.414 (2) Å | Cell parameters from 50 reflections |
b = 11.041 (2) Å | θ = 2.1–25.0° |
c = 12.347 (2) Å | µ = 3.83 mm−1 |
α = 105.83 (3)° | T = 290 K |
β = 103.87 (3)° | Prism, yellow |
γ = 107.40 (3)° | 0.4 × 0.3 × 0.2 mm |
V = 1103.7 (6) Å3 | |
Data collection top
Kuma KM4 diffractometer | 1691 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
θ/2θ scans | h = −10→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.280, Tmax = 0.465 | l = 0→14 |
4059 measured reflections | 3 standard reflections every 200 reflections |
3860 independent reflections | intensity decay: 3.0% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0687P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
3860 reflections | Δρmax = 0.59 e Å−3 |
309 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0042 (11) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.0728 (6) | 0.8038 (6) | 0.5273 (5) | 0.0356 (14) | |
H1 | 0.1605 | 0.7989 | 0.5072 | 0.043* | |
C2 | 0.0642 (8) | 0.7963 (6) | 0.6335 (5) | 0.0443 (16) | |
H2 | 0.1439 | 0.7833 | 0.6844 | 0.053* | |
C3 | −0.0681 (7) | 0.8039 (6) | 0.6667 (6) | 0.0423 (15) | |
H3 | −0.0732 | 0.7999 | 0.7400 | 0.051* | |
C4 | −0.1884 (7) | 0.8172 (6) | 0.5919 (5) | 0.0431 (16) | |
H4 | −0.2735 | 0.8243 | 0.6152 | 0.052* | |
C5 | −0.4131 (7) | 0.8916 (6) | 0.2332 (6) | 0.0514 (17) | |
H5 | −0.4970 | 0.8981 | 0.2583 | 0.062* | |
C6 | −0.4029 (8) | 0.9078 (7) | 0.1302 (6) | 0.0542 (18) | |
H6 | −0.4739 | 0.9383 | 0.0908 | 0.065* | |
C7 | −0.2829 (8) | 0.8906 (7) | 0.0883 (6) | 0.0530 (17) | |
H7 | −0.2893 | 0.8902 | 0.0118 | 0.064* | |
C8 | −0.1687 (8) | 0.8610 (6) | 0.1509 (5) | 0.0432 (15) | |
H8 | −0.0861 | 0.8535 | 0.1244 | 0.052* | |
C9 | −0.0505 (6) | 0.8233 (6) | 0.3345 (5) | 0.0327 (13) | |
N10 | −0.3046 (5) | 0.8388 (5) | 0.4052 (4) | 0.0379 (12) | |
C11 | −0.0496 (6) | 0.8179 (5) | 0.4481 (5) | 0.0325 (14) | |
C12 | −0.1836 (6) | 0.8249 (6) | 0.4817 (5) | 0.0324 (13) | |
C13 | −0.1713 (6) | 0.8449 (6) | 0.2622 (5) | 0.0352 (14) | |
C14 | −0.2975 (6) | 0.8585 (5) | 0.3009 (5) | 0.0354 (14) | |
C15 | 0.0815 (7) | 0.8046 (6) | 0.2922 (5) | 0.0330 (13) | |
O16 | 0.0220 (4) | 0.6975 (4) | 0.1885 (3) | 0.0352 (9) | |
O17 | 0.2197 (5) | 0.8733 (4) | 0.3464 (4) | 0.0489 (11) | |
C18 | 0.1277 (6) | 0.6491 (5) | 0.1441 (5) | 0.0358 (14) | |
C19 | 0.1773 (7) | 0.6845 (6) | 0.0573 (5) | 0.0412 (15) | |
C20 | 0.2626 (7) | 0.6224 (7) | 0.0050 (6) | 0.0509 (17) | |
H20 | 0.2929 | 0.6445 | −0.0558 | 0.061* | |
C21 | 0.2996 (8) | 0.5247 (7) | 0.0405 (6) | 0.0564 (18) | |
H21 | 0.3556 | 0.4812 | 0.0034 | 0.068* | |
C22 | 0.2557 (7) | 0.4911 (6) | 0.1291 (6) | 0.0520 (17) | |
H22 | 0.2828 | 0.4264 | 0.1543 | 0.062* | |
C23 | 0.1668 (7) | 0.5521 (5) | 0.1814 (5) | 0.0336 (13) | |
Br24 | 0.13315 (9) | 0.82219 (8) | 0.01180 (7) | 0.0651 (3) | |
Br25 | 0.10690 (10) | 0.50960 (8) | 0.30427 (7) | 0.0682 (3) | |
C26 | −0.4511 (7) | 0.8276 (8) | 0.4348 (6) | 0.062 (2) | |
H26A | −0.5274 | 0.8345 | 0.3720 | 0.092* | 0.50 |
H26B | −0.4253 | 0.9001 | 0.5093 | 0.092* | 0.50 |
H26C | −0.4950 | 0.7410 | 0.4421 | 0.092* | 0.50 |
H26D | −0.4377 | 0.8159 | 0.5103 | 0.092* | 0.50 |
H26E | −0.5399 | 0.7503 | 0.3729 | 0.092* | 0.50 |
H26F | −0.4701 | 0.9094 | 0.4402 | 0.092* | 0.50 |
S27 | 0.47817 (19) | 0.74668 (17) | 0.74315 (14) | 0.0462 (4) | |
O28 | 0.4471 (6) | 0.7982 (5) | 0.6488 (4) | 0.0712 (14) | |
O29 | 0.6397 (5) | 0.7615 (5) | 0.7907 (4) | 0.0647 (13) | |
O30 | 0.4055 (5) | 0.7810 (5) | 0.8293 (4) | 0.0598 (13) | |
C31 | 0.3736 (9) | 0.5637 (8) | 0.6686 (7) | 0.067 (2) | |
F32 | 0.4299 (7) | 0.5121 (5) | 0.5889 (5) | 0.116 (2) | |
F33 | 0.3768 (6) | 0.5002 (5) | 0.7442 (5) | 0.0994 (16) | |
F34 | 0.2197 (6) | 0.5292 (5) | 0.6071 (5) | 0.0982 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.029 (3) | 0.039 (4) | 0.049 (4) | 0.024 (3) | 0.015 (3) | 0.018 (3) |
C2 | 0.052 (4) | 0.039 (4) | 0.037 (4) | 0.023 (3) | 0.003 (3) | 0.012 (3) |
C3 | 0.050 (4) | 0.040 (4) | 0.043 (4) | 0.019 (3) | 0.022 (3) | 0.016 (3) |
C4 | 0.041 (4) | 0.043 (4) | 0.050 (4) | 0.018 (3) | 0.024 (3) | 0.015 (3) |
C5 | 0.032 (3) | 0.053 (4) | 0.066 (5) | 0.023 (3) | 0.009 (3) | 0.017 (4) |
C6 | 0.047 (4) | 0.050 (4) | 0.063 (5) | 0.024 (4) | 0.007 (4) | 0.023 (4) |
C7 | 0.055 (4) | 0.050 (4) | 0.051 (4) | 0.023 (4) | 0.008 (4) | 0.020 (4) |
C8 | 0.048 (4) | 0.045 (4) | 0.039 (3) | 0.024 (3) | 0.012 (3) | 0.017 (3) |
C9 | 0.026 (3) | 0.031 (3) | 0.036 (3) | 0.012 (3) | 0.006 (3) | 0.008 (3) |
N10 | 0.028 (3) | 0.037 (3) | 0.049 (3) | 0.016 (2) | 0.016 (3) | 0.009 (3) |
C11 | 0.032 (3) | 0.021 (3) | 0.036 (4) | 0.008 (3) | 0.011 (3) | 0.002 (3) |
C12 | 0.026 (3) | 0.033 (3) | 0.030 (3) | 0.009 (3) | 0.007 (3) | 0.005 (3) |
C13 | 0.027 (3) | 0.030 (4) | 0.048 (4) | 0.014 (3) | 0.011 (3) | 0.012 (3) |
C14 | 0.020 (3) | 0.021 (3) | 0.049 (4) | 0.005 (3) | 0.002 (3) | 0.003 (3) |
C15 | 0.031 (4) | 0.026 (3) | 0.034 (3) | 0.011 (3) | 0.004 (3) | 0.008 (3) |
O16 | 0.025 (2) | 0.037 (2) | 0.044 (2) | 0.0152 (19) | 0.013 (2) | 0.011 (2) |
O17 | 0.026 (3) | 0.052 (3) | 0.057 (3) | 0.014 (2) | 0.010 (2) | 0.007 (2) |
C18 | 0.027 (3) | 0.032 (4) | 0.041 (4) | 0.010 (3) | 0.013 (3) | 0.003 (3) |
C19 | 0.036 (3) | 0.038 (4) | 0.047 (4) | 0.013 (3) | 0.014 (3) | 0.014 (3) |
C20 | 0.043 (4) | 0.054 (4) | 0.054 (4) | 0.015 (4) | 0.027 (4) | 0.014 (4) |
C21 | 0.041 (4) | 0.043 (4) | 0.067 (5) | 0.013 (4) | 0.017 (4) | 0.000 (4) |
C22 | 0.046 (4) | 0.041 (4) | 0.072 (5) | 0.025 (4) | 0.024 (4) | 0.014 (4) |
C23 | 0.041 (4) | 0.022 (3) | 0.031 (3) | 0.007 (3) | 0.011 (3) | 0.009 (3) |
Br24 | 0.0783 (6) | 0.0685 (6) | 0.0799 (6) | 0.0395 (5) | 0.0442 (5) | 0.0470 (5) |
Br25 | 0.0994 (7) | 0.0650 (6) | 0.0727 (6) | 0.0481 (5) | 0.0465 (5) | 0.0411 (5) |
C26 | 0.040 (4) | 0.086 (6) | 0.067 (5) | 0.033 (4) | 0.032 (4) | 0.021 (4) |
S27 | 0.0489 (11) | 0.0536 (11) | 0.0455 (9) | 0.0265 (9) | 0.0225 (9) | 0.0197 (8) |
O28 | 0.083 (4) | 0.087 (4) | 0.070 (3) | 0.047 (3) | 0.035 (3) | 0.045 (3) |
O29 | 0.042 (3) | 0.076 (4) | 0.069 (3) | 0.024 (3) | 0.016 (2) | 0.018 (3) |
O30 | 0.068 (3) | 0.073 (3) | 0.051 (3) | 0.041 (3) | 0.030 (3) | 0.020 (3) |
C31 | 0.046 (5) | 0.063 (6) | 0.071 (5) | 0.012 (4) | 0.016 (4) | 0.009 (5) |
F32 | 0.127 (4) | 0.082 (4) | 0.117 (4) | 0.033 (3) | 0.074 (4) | −0.013 (3) |
F33 | 0.115 (4) | 0.064 (3) | 0.128 (4) | 0.036 (3) | 0.041 (3) | 0.050 (3) |
F34 | 0.066 (3) | 0.103 (4) | 0.090 (4) | 0.015 (3) | 0.017 (3) | 0.014 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.355 (8) | C15—O17 | 1.196 (6) |
C1—C11 | 1.400 (7) | O16—C18 | 1.413 (6) |
C1—H1 | 0.9300 | C18—C19 | 1.371 (8) |
C2—C3 | 1.419 (8) | C18—C23 | 1.385 (8) |
C2—H2 | 0.9306 | C19—C20 | 1.367 (8) |
C3—C4 | 1.353 (8) | C19—Br24 | 1.879 (6) |
C3—H3 | 0.9300 | C20—C21 | 1.373 (9) |
C4—C12 | 1.397 (8) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C22 | 1.362 (9) |
C5—C6 | 1.354 (9) | C21—H21 | 0.9300 |
C5—C14 | 1.409 (8) | C22—C23 | 1.389 (8) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—C7 | 1.391 (9) | C23—Br25 | 1.865 (5) |
C6—H6 | 0.9300 | C26—H26A | 0.9600 |
C7—C8 | 1.345 (8) | C26—H26B | 0.9600 |
C7—H7 | 0.9300 | C26—H26C | 0.9600 |
C8—C13 | 1.438 (8) | C26—H26D | 0.9600 |
C8—H8 | 0.9300 | C26—H26E | 0.9600 |
C9—C13 | 1.393 (7) | C26—H26F | 0.9600 |
C9—C11 | 1.417 (7) | S27—O30 | 1.424 (4) |
C9—C15 | 1.505 (8) | S27—O29 | 1.433 (5) |
N10—C12 | 1.371 (7) | S27—O28 | 1.437 (5) |
N10—C14 | 1.376 (7) | S27—C31 | 1.805 (8) |
N10—C26 | 1.488 (7) | C31—F32 | 1.303 (8) |
C11—C12 | 1.436 (7) | C31—F33 | 1.311 (9) |
C13—C14 | 1.415 (8) | C31—F34 | 1.344 (9) |
C15—O16 | 1.336 (7) | | |
| | | |
C2—C1—C11 | 120.4 (5) | C20—C19—C18 | 120.4 (6) |
C2—C1—H1 | 119.5 | C20—C19—Br24 | 119.3 (5) |
C11—C1—H1 | 120.1 | C18—C19—Br24 | 120.3 (4) |
C1—C2—C3 | 120.7 (6) | C19—C20—C21 | 119.6 (6) |
C1—C2—H2 | 120.0 | C19—C20—H20 | 120.1 |
C3—C2—H2 | 119.2 | C21—C20—H20 | 120.2 |
C4—C3—C2 | 120.3 (6) | C22—C21—C20 | 120.9 (6) |
C4—C3—H3 | 119.2 | C22—C21—H21 | 119.8 |
C2—C3—H3 | 120.6 | C20—C21—H21 | 119.4 |
C3—C4—C12 | 120.6 (5) | C21—C22—C23 | 119.9 (6) |
C3—C4—H4 | 119.7 | C21—C22—H22 | 120.8 |
C12—C4—H4 | 119.7 | C23—C22—H22 | 119.3 |
C6—C5—C14 | 119.1 (6) | C18—C23—C22 | 119.1 (5) |
C6—C5—H5 | 121.4 | C18—C23—Br25 | 120.1 (4) |
C14—C5—H5 | 119.5 | C22—C23—Br25 | 120.8 (5) |
C5—C6—C7 | 121.8 (6) | N10—C26—H26A | 109.5 |
C5—C6—H6 | 117.9 | N10—C26—H26B | 109.5 |
C7—C6—H6 | 120.1 | H26A—C26—H26B | 109.5 |
C8—C7—C6 | 121.2 (6) | N10—C26—H26C | 109.5 |
C8—C7—H7 | 120.0 | H26A—C26—H26C | 109.5 |
C6—C7—H7 | 118.5 | H26B—C26—H26C | 109.5 |
C7—C8—C13 | 119.7 (6) | N10—C26—H26D | 109.5 |
C7—C8—H8 | 120.9 | H26A—C26—H26D | 141.1 |
C13—C8—H8 | 119.4 | H26B—C26—H26D | 56.3 |
C13—C9—C11 | 121.1 (5) | H26C—C26—H26D | 56.3 |
C13—C9—C15 | 120.0 (5) | N10—C26—H26E | 109.5 |
C11—C9—C15 | 119.0 (5) | H26A—C26—H26E | 56.3 |
C12—N10—C14 | 122.6 (4) | H26B—C26—H26E | 141.1 |
C12—N10—C26 | 118.3 (5) | H26C—C26—H26E | 56.3 |
C14—N10—C26 | 119.0 (5) | H26D—C26—H26E | 109.5 |
C1—C11—C9 | 123.6 (5) | N10—C26—H26F | 109.5 |
C1—C11—C12 | 118.8 (5) | H26A—C26—H26F | 56.3 |
C9—C11—C12 | 117.6 (5) | H26B—C26—H26F | 56.3 |
N10—C12—C4 | 121.2 (5) | H26C—C26—H26F | 141.1 |
N10—C12—C11 | 119.6 (5) | H26D—C26—H26F | 109.5 |
C4—C12—C11 | 119.3 (5) | H26E—C26—H26F | 109.5 |
C9—C13—C14 | 119.7 (5) | O30—S27—O29 | 115.9 (3) |
C9—C13—C8 | 122.1 (5) | O30—S27—O28 | 114.1 (3) |
C14—C13—C8 | 118.2 (5) | O29—S27—O28 | 114.5 (3) |
N10—C14—C5 | 121.1 (5) | O30—S27—C31 | 103.3 (3) |
N10—C14—C13 | 118.8 (5) | O29—S27—C31 | 102.5 (3) |
C5—C14—C13 | 120.1 (6) | O28—S27—C31 | 104.2 (4) |
C9—C15—O16 | 110.1 (5) | F32—C31—F33 | 108.5 (7) |
C9—C15—O17 | 124.5 (5) | F32—C31—F34 | 105.1 (7) |
C15—O16—C18 | 118.7 (4) | F33—C31—F34 | 106.6 (7) |
O16—C15—O17 | 125.4 (5) | F32—C31—S27 | 112.2 (6) |
C19—C18—C23 | 120.1 (5) | F33—C31—S27 | 112.4 (6) |
C19—C18—O16 | 121.8 (5) | F34—C31—S27 | 111.6 (6) |
C23—C18—O16 | 117.7 (5) | | |
| | | |
C11—C1—C2—C3 | −0.6 (9) | C8—C13—C14—N10 | 177.8 (5) |
C1—C2—C3—C4 | 0.8 (9) | C9—C13—C14—C5 | 174.8 (5) |
C2—C3—C4—C12 | −0.6 (9) | C8—C13—C14—C5 | −2.2 (8) |
C14—C5—C6—C7 | 1.0 (10) | C13—C9—C15—O17 | 123.5 (6) |
C5—C6—C7—C8 | −2.0 (11) | C13—C9—C15—O16 | −58.9 (6) |
C6—C7—C8—C13 | 0.8 (10) | C11—C9—C15—O16 | 120.9 (5) |
C2—C1—C11—C9 | −178.5 (6) | O17—C15—O16—C18 | 8.0 (8) |
C2—C1—C11—C12 | 0.3 (8) | C9—C15—O16—C18 | −169.6 (5) |
C13—C9—C11—C1 | −176.4 (5) | C11—C9—C15—O17 | −56.7 (8) |
C15—C9—C11—C1 | 3.8 (8) | C15—O16—C18—C19 | −98.7 (6) |
C13—C9—C11—C12 | 4.7 (8) | C15—O16—C18—C23 | 88.3 (6) |
C15—C9—C11—C12 | −175.1 (5) | C23—C18—C19—C20 | 1.4 (9) |
C14—N10—C12—C4 | 174.3 (5) | O16—C18—C19—C20 | −171.4 (5) |
C26—N10—C12—C4 | −7.7 (8) | C23—C18—C19—Br24 | −177.0 (4) |
C14—N10—C12—C11 | −5.9 (8) | O16—C18—C19—Br24 | 10.2 (8) |
C26—N10—C12—C11 | 172.2 (5) | C18—C19—C20—C21 | −0.5 (9) |
C3—C4—C12—N10 | −179.8 (6) | Br24—C19—C20—C21 | 178.0 (5) |
C3—C4—C12—C11 | 0.4 (9) | C19—C20—C21—C22 | −1.6 (10) |
C1—C11—C12—N10 | 180.0 (5) | C20—C21—C22—C23 | 2.6 (10) |
C9—C11—C12—N10 | −1.1 (8) | C19—C18—C23—C22 | −0.4 (9) |
C1—C11—C12—C4 | −0.2 (8) | O16—C18—C23—C22 | 172.8 (5) |
C9—C11—C12—C4 | 178.7 (5) | C19—C18—C23—Br25 | 177.3 (4) |
C11—C9—C13—C14 | −1.6 (8) | O16—C18—C23—Br25 | −9.6 (7) |
C15—C9—C13—C14 | 178.2 (5) | C21—C22—C23—C18 | −1.6 (9) |
C11—C9—C13—C8 | 175.3 (5) | C21—C22—C23—Br25 | −179.3 (5) |
C15—C9—C13—C8 | −5.0 (8) | O30—S27—C31—F32 | −177.0 (6) |
C7—C8—C13—C9 | −175.7 (6) | O29—S27—C31—F32 | −56.2 (7) |
C7—C8—C13—C14 | 1.2 (9) | O28—S27—C31—F32 | 63.5 (7) |
C12—N10—C14—C5 | −170.9 (5) | O30—S27—C31—F33 | −54.4 (6) |
C26—N10—C14—C5 | 11.1 (8) | O29—S27—C31—F33 | 66.4 (6) |
C12—N10—C14—C13 | 9.1 (8) | O28—S27—C31—F33 | −174.0 (5) |
C26—N10—C14—C13 | −168.9 (5) | O30—S27—C31—F34 | 65.3 (6) |
C6—C5—C14—N10 | −178.9 (6) | O29—S27—C31—F34 | −173.9 (6) |
C6—C5—C14—C13 | 1.1 (9) | O28—S27—C31—F34 | −54.2 (6) |
C9—C13—C14—N10 | −5.2 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O29i | 0.93 | 2.52 | 3.362 (8) | 150 |
C20—H20···O30ii | 0.93 | 2.52 | 3.413 (8) | 161 |
C22—H22···O29iii | 0.93 | 2.59 | 3.523 (9) | 176 |
Symmetry codes: (i) x−1, y, z−1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1. |
π–π interactions (Å,°) in (I) topCgI | CgJ | Cg···Cg | Dihedral angle | Interplanar dist. | Offset |
1 | 1iv | 3.968 (3) | 0.0 | 3.515 (4) | 1.841 (4) |
1 | 2iv | 3.610 (4) | 2.1 | 3.468 (4) | 1.003 (4) |
2 | 1iv | 3.610 (4) | 2.1 | 3.458 (4) | 1.037 (4) |
2 | 3iv | 3.836 (4) | 7.1 | 3.500 (4) | 1.570 (4) |
3 | 2iv | 3.835 (4) | 7.1 | 3.281 (4) | 1.986 (4) |
4 | 4v | 3.719 (4) | 0.0 | 3.462 (4) | 1.358 (4) |
Symmetry codes: (iv) -x, 2-y, 1-z; (v) -x, 1-y, -z.
Cg represents the centre of gravity of the rings, as follows: Cg1 ring
C9/C11/C12/N10/C14/C13, Cg2 ring C1–C4/C12/C11, Cg3 ring C5–C8/C13/C14
and Cg4 ring C18–C23.
Cg···Cg is the distance between ring centroids. The dihedral angle is that
between the planes of CgI and CgJ. The interplanar distance is the
perpendicular distance of CgI from ring J. Offset is the perpendicular
distance of ring I from ring J. |